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ORGANIC SPECTROSCOPY

Read all about Organic Spectroscopy on ORGANIC SPECTROSCOPY INTERNATIONAL 

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK LIFE SCIENCES LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 PLUS year tenure till date June 2021, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 33 lakh plus views on New Drug Approvals Blog in 233 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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DR SRINIVASA REDDY gets NASI – Reliance Industries Platinum Jubilee Award (2015) for Application Oriented Innovations in Physical Sciences.


 

DR REDDY

DR SRINIVASA REDDY  recieving NASI – Reliance Industries Platinum Jubilee Award (2015) for Application Oriented Innovations in Physical Sciences.

Dr. D. Srinivasa Reddy, Senior Scientist, Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune – 411 008

AWARD CLICK HERE….LINK

PUNE: Senior scientist of National Chemical Laboratory (NCL), D Srinivasa Reddy has been selected for this year’s NASI-Reliance Industries Platinum Jubilee award for the application oriented innovations in the area of physical sciences instituted by the National Academy of Sciences, India (NASI). Two awards each in physical sciences and two in biological sciences are given every year, a statement issued by NCL said.

Manindra Agrawal from Department of Computer Science and Engineering, Indian Institute of Kanpur is the other recipient of this award in physical sciences. Each award carries a plaque and Rs 2 lakh cash.

The award will be presented in the 85th annual session of National Academy of Sciences, India. Reddy’s research group interests are in the field of total synthesis and drug discovery by applying medicinal chemistry. He has also been involved in the synthesis of the agrochemicals like small molecules for crop protection, said the statement. The total synthesis of more than 20 natural products has been achieved in his lab including a sex pheromone that attracts the mealy bugs and has potential use in the crop protection.

On the medicinal chemistry front significant progress has been made by his group using a new concept called silicon-switch approach towards central nervous system drugs. Identification of new chemical entities for the potential treatment of diabetes and infectious diseases is being done in collaboration with industry partners.

Read about DR REDDY  at 

click

One Organic Chemist One Day: Dr. D. Srinivasa Reddy of …

oneorganichemistoneday.blogspot.com/2015/02/dr-d-srinivasa-reddy.html

Feb 23, 2015 – Dr. Reddy’s research group current interests are in the field of total synthesis and drug discovery by applying medicinal chemistry

Dr. D. Srinivasa Reddy of NCL winner Shanti Swarup Bhatnagar Award 2015

 

Some details

The National Academy of Sciences, India (NASI) 5, Lajpatrai Road, Allahabad – 211002 NASI-RELIANCE INDUSTRIES PLATINUM JUBILEE AWARDS FOR THE YEAR 2015 FOR APPLICATION ORIENTED INNOVATIONS COVERING BOTH PHYSICAL AND BIOLOGICAL SCIENCES NASI invites nominations for the NASI-Reliance Industries Platinum Jubilee Awards for APPLICATION ORIENTED INNOVATIONS for the year 2015. The nominee should be an Indian citizen / Overseas Citizen of India working in India and below the age of 50 years as on April 15, 2015. Areas for the Awards – Physical Sciences, including – Chemistry, Engineering, Mathematics, Physics, Electronics, Nanotechnology, Information & Computer Sciences, Earth and Atmospheric Sciences; Biological Sciences, including – Agriculture, Animal and Plant Sciences, Environment, Biotechnology, Biochemistry, Bioprocess Engineering, Bioinformatics, all branches of medical sciences and Nanotechnology. Number and Value of Awards – two in Physical Sciences and two in Biological Sciences each year. Each award carries a Plaque and Rs. 2 lakhs in cash. Nominators and Last Date – All Science Secretaries, Secretary HRD, Director Generals – CSIR, ICMR & ICAR; Directors of IITs, IIITs, National Laboratories, Industries with well recognized R&D units including private research institutions; Vice-Chancellors of all Universities – Central & State; Directors of Indian Institute of Science, Bangalore, AIIMS, New Delhi, PGI’s of Medical Research, Chairman, UGC; Presidents of all Science and Engineering Academies (Engineering, Medical, Agriculture); All Fellows of the NASI. The nomination shall be made in the prescribed format. Twenty (20) copies of the nomination form along with only one soft copy (in CD), complete in all respect with the supporting documents, must reach the Academy latest by April 15, 2015. A candidate may only be nominated once. However, a nomination will remain valid for consideration for 3 years or the age eligibility which ever expires earlier. Selection of the Awardees – As per Regulations of NASI Presentation of the Awards – The presentation of the Awards will be made at the time of 85 th Annual Session of NASI. Details and Nomination form for the award are also available on NASI’s website http://www.nasi.org.in and http://www.nasi.nic.in …………….http://www.nasi.org.in/NASI-Reliance%20Industries%20Platinum%20Jubilee%20Awards%202015.pdf

SEE

http://www.nasi.org.in/NASI-Reliance%20Industries%20Platinum%20Jubilee%20Awardees%20(2015).htm

PUNE: Senior scientist at National Chemical Laboratory (NCL) D Srinivasa Reddy has bagged yet another award, the NASI-Reliance Industries Platinum Jubilee award for the year 2015.

This is the second award Reddy has won in a span of less than a fortnight. Earlier, he was selected for the bronze medal presented by the Chemical Research Society of India (CRSI). He has also been a recipient of excellence award from the National Drug Research Institute.

The platinum jubilee award is being conferred for his work in application-oriented innovations in physical sciences category.

Every year, this award recognises two scientists, each working in the fields of physical and biological sciences.

The other scientist who has been awarded in this category is Manindra Agarwal from IIT, Kanpur.

Reddy along with his team has been involved in several high-end research in drug discovery, mainly by applying medicinal chemistry. Other major works he undertook also involve synthesising of agrochemicals meant to be used for crop protection.

He also has vast experience working with various pharmaceutical companies prior to joining NCL in 2010.

The award consists of cash of Rs 2 lakh.

NASI

National Academy of Sciences, India (www.nasi.org.in) was founded in 1930 with the objective to provide a national forum for the scientists to help them publish their research work and discuss the issues for the solutions. NASI-Reliance together give two awards each in the areas of physical and biological sciences for the application oriented innovations started from the year 2006. Areas for the Awards – Physical Sciences, including Chemistry, Engineering, Mathematics, Physics, Electronics, Nanotechnology, Information & Computer Sciences, Earth and Atmospheric Sciences; Biological Sciences, including Agriculture, Animal and Plant Sciences, Environment, Biotechnology, Biochemistry, Bioprocess Engineering, Bioinformatics, all branches of medical sciences and Nanotechnology.

 

Read about DR REDDY  at

One Organic Chemist One Day: Dr. D. Srinivasa Reddy of …

oneorganichemistoneday.blogspot.com/2015/02/dr-d-srinivasa-reddy.html

Feb 23, 2015 – Dr. Reddy’s research group current interests are in the field of total synthesis and drug discovery by applying medicinal chemistry

Dr. D. Srinivasa Reddy of NCL winner Shanti Swarup Bhatnagar Award 2015

 

 

Some pictures of his group


NCL, PUNE

//////////DR SRINIVASA REDDY , NASI – Reliance Industries Platinum Jubilee Award, 2015, Application Oriented Innovations in Physical Sciences,

SILICO LINEZOLID, SILINEZOLID, NDS 10024


Therapeutic options for brain infections caused by pathogens with a reduced sensitivity to drugs are limited. Recent reports on the potential use of linezolid in treating brain infections prompted us to design novel compounds around this scaffold. Herein, we describe the design and synthesis of various oxazolidinone antibiotics with the incorporation of silicon.

Our findings in preclinical species suggest that silicon incorporation is highly useful in improving brain exposures. Interestingly, three compounds from this series demonstrated up to a 30-fold higher brain/plasma ratio when compared to linezolid thereby indicating their therapeutic potential in brain associated disorders

Design, Synthesis, and Identification of Silicon Incorporated Oxazolidinone Antibiotics with Improved Brain Exposure

CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India
Daiichi Sankyo India Pharma Pvt. Ltd., Gurgaon, Haryana 122015, India
§ Incozen Therapeutics Pvt. Ltd., Alexandria Knowledge Park, Turkapally, Rangareddy 500078, India
ACS Med. Chem. Lett., Article ASAP
DOI: 10.1021/acsmedchemlett.5b00213
Publication Date (Web): October 26, 2015
Copyright © 2015 American Chemical Society
 str1
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SILINEZOLID, NDS 10024
CAS 1430321-45-1
C18 H26 F N3 O3 Si, 379.50
Acetamide, N-​[[(5S)​-​3-​[4-​(4,​4-​dimethyl-​1-​aza-​4-​silacyclohex-​1-​yl)​-​3-​fluorophenyl]​-​2-​oxo-​5-​oxazolidinyl]​methyl]​-
str1
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Examples from patent

Figure US20140296133A1-20141002-C00027
    (S)—N((3-(4-(4,4-dimethyl-1,4-azasilinan-1-yl)-3-fluorophenyl)-2 oxooxazolidin-5-yl)methyl)acetamide
    NDS 10024
Patent   US20140296133
SEE
AUTHORS
    Preparation of (S)—N((3-(4-(4,4-dimethyl-1,4-azasilinan-1-yl)-3-fluorophenyl)-2 oxooxazolidin-5-yl)methyl)acetamide (12)

  • Figure US20140296133A1-20141002-C00027
  • To a solution of 8 (50 mg, 0.135 mmol) in dimethylformamide (DMF), lithium-t-butoxide (LiOtBu) (32.3 mg, 0.4 mmol) is added. The mixture is stirred at 25° C. for 15 min, followed by the addition of MeOH (0.01 mL, 0.27 mmol). 6 (52 mg, 0.27 mmol) is then added and the reaction mixture is allowed to stir at 25° C. for 24 h. Glacial acetic acid is then added and the organic phase is extracted with EtOAc and washed with brine solution. The crude material is purified by column chromatography on silica gel using hexane-EtOAC mixtures to furnish the pure product 12. The analogous procedure for the corresponding morpholine analogue was adapted from Lu, C. V.; Chen, J. J.; Perrault, W. R.; Conway, B. G.; Maloney, M. T.; Wang, Y. Org. Pro. Res. and Development. 2006, 10, 272-277.
  • 1H NMR (200 MHz, CDCl3): δ 7.33 (d, J=13.8 Hz, 1H), 7.02-6.94 (m, 2H), 6.52 (t, J=5.8 Hz, 1H), 4.77-4.73 (m, 1H), 3.99 (t, J=9.04 Hz, 1H), 3.72 (dd, J=9.0 Hz, 6.8 Hz, 1H), 3.69-3.58 (m, 2H), 3.31 (t, J=5.5 Hz, 4H), 2.01 (s, 3H), 0.89 (t, J=5.5 Hz, 4H), 0.10 (s, 6H). 13C NMR (100 MHz, CDCl3): δ171.2, 155.0 (d, J=244.3 Hz), 154.5, 138.2 (d, J=9.3 Hz), 131.5, 119.9, 114.0 (d, J=3.4 Hz), 107.6 (d, J=27.1 Hz), 71.9, 50.9, 47.7, 41.9, 23.0, 14.3, −2.9.
    Preparation of Bis(bromomethyl)dimethylsilane (2) (as per scheme 2)

  • Figure US20140296133A1-20141002-C00028
  • HBr gas is bubbled to a solution of dimethyl divinylsilane 1 (10.0 g, 89.28 mmols), and dibenzoylperoxide (DBP, 100 mg), in heptane (100 mL) at 0° C. for 30 min. The Reaction mixture (RM) is allowed to stir at room temperature (25° C.) for 18 h, water (200 mL) is added to the reaction mixture and the organic layer is separated. The heptane layer is washed with 2N NaOH (2 100 mL), dried and concentrated to obtain the product 2 as a colourless liquid (24.5 g) in 100% yield.
  • 1H NMR (200 MHz, CDCl3): δ 3.58-3.49 (m, 4H), 1.45-1.40 (m, 4H), 0.09 (s, 6H).
      Preparation of 1-benzyl-4,4-dimethyl-1,4-azasilinane (3)

    • Figure US20140296133A1-20141002-C00029
    • Benzylamine (20 mL, 182 mmol) and Et3N (15.2 mL, 109 mmol) are added to a solution of bis-(bromomethyl) dimethylsilane 2 (10 g, 36.5 mmol) in chloroform (100 mL). The mixture is then refluxed for 16 h. 5% sodiumhydroxide solution (150 mL) is then added and the aqueous layer is extracted with dichloromethane (DCM, 2×100 mL). It is then washed with brine (200 mL), dried and concentrated. The product is purified by column chromatography on silica gel using hexane-EtOAc mixtures to obtain the product 3 as a light yellow liquid (4.3 g) in 54% yield.
    • 1H NMR (200 MHz, CDCl3): δ 7.23-7.35 (m, 5H), 3.66 (s, 2H), 2.68 (t, J=6.3 Hz, 4H), 0.75 (t, J=6.3 Hz, 4H), 0.04 (s, 6H).

Preparation of 4,4-dimethyl-1,4-azasilinane hydrochloride (4)

    • Figure US20140296133A1-20141002-C00030
    • To a solution of 4,4-dimethyl-1,4-azasilinane 3 (2.3 g, 10.5 mmol) in EtOH (20 mL), 6N hydrochloricacid (1.75 mL, 10.5 mmol) is added and the solvent is removed under reduced pressure. The reaction mixture is co-evaporated with EtOH (2×10 mL) and recrystallized from EtOH-diethyl ether. To a slurry of Pd/C (50 mg) in EtOH (15 mL) an ethanolic solution of above prepared HCl salt is added drop wise and stirred at 25° C. under hydrogen atmosphere for 20 h. The reaction mixture is filtered through celite and washed with 2×20 mL of MeOH. The filtrate is then concentrated under reduced pressure to give viscous oil which was triturated with diethyl ether to obtain the product 4 as a white solid (950 mg) in 70% yield.

Preparation of 1-(2-fluoro-4-nitrophenyl)-4,4-dimethyl-1,4-azasilinane (9)

    • Figure US20140296133A1-20141002-C00031
    • To a solution of 4,4-dimethyl-1,4-azasilinane hydrochloride 4 (500 mg, 3.85 mmol) in EtOAc (15 mL), triethylamine (1.3 mL, 9.63 mmol) is added and stirred at 25° C. for 10 min. The reaction mixture is cooled to 0° C. and 3,4-difluoronitrobenzene (612 mg, 3.85 mmol) is added drop wise and allowed to stir at 25° C. for 6 h. Water is then added and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×10 mL) and the solvent is removed under reduced pressure. The product is purified by column chromatography using hexane-EtOAc mixtures and a crystalline yellow solid 9 (721 mg) is obtained in 70% yield.
    • 1H NMR (200 MHz, CDCl3): δ 7.93-7.84 (m, 2H), 6.86 (t, J=4 Hz, 1H), 3.70-3.67 (m, 4H), 0.91-0.85 (m, 4H), 0.12 (s, 6H). 13C NMR (50 MHz, CDCl3): δ 151.1 (d, J=246.71 Hz), 144.4 (d, J=7.13 Hz), 137.8 (d, J=8.59 Hz), 121.4, 115.9 (d, J=4.61 Hz), 113.2 (J=27.78 Hz), 49.4, 13.8, −2.8. IR (CHCl3): ν 2948, 2894, 1603, 1523, 1492, 1400, 1342, 1223, 983, 832, 742 cm−1′. M.P: 70-72° C.

Preparation of benzyl 4-(4,4-dimethyl-1,4-azasilinan-1-yl)-3-fluorophenylcarbamate (10)

    • Figure US20140296133A1-20141002-C00032
    • To a solution of compound 9 (610 mg, 2.28 mmol) in THF (25 mL), Pd/C (30 mg) is added and hydrogenated under a pressure of 35 psi in a par hydrogenator for 8 h. The reaction mixture is filtered through celite. Celite pad is washed with THF (2×20 mL). To the filtrate, saturated NaHCO3 (420 mg, 5.01 mmol) and CBzCl (427 mg, 2.5 mmol) are added at 0° C. and stirred at 25° C. for 5 h. 10 mL water is added to reaction mixture and the aqueous layer is extracted with EtOAc (2×20 mL). The crude mixture is then subjected to column chromatography on silica gel using hexane-EtOAc mixtures to afford the product as a viscous liquid 10 (690 mg) in 82% yield.
    • 1H NMR (200 MHz, CDCl3): δ 7.41-7.37 (m, 5H), 6.94-6.93 (m, 2H), 6.68 (s, 1H), 5.21 (s, 1H), 3.3 (t, J=6.38 Hz, 4H), 0.93 (t, J=6.08 Hz, 4H), −0.13 (s, 6H). 13C NMR (50 MHz, CDCl3): 155.4 (d, 244.4 Hz), 153.6, 136.1, 135.9, 128.6, 128.5, 128.3, 120.4, 117.2 (d, 18.7 Hz), 114.7, 108.3 (20.5 Hz), 67.1, 51.4, 14.4, −3.0. IR (CHCl3): ν 3317, 2953, 2803, 1706, 1594, 1521, 1271, 1221, 1058, 869, 759 cm−1. M.P: 80-82° C.

Preparation of (S)-5-(aminomethyl)-3-(4-(4,4-dimethyl-1,4-azasilinan-1-yl)-3-fluorophenyl)oxazolidin-2-one (11) (NDS-10057)

    • Figure US20140296133A1-20141002-C00033
    • To a solution of 10 (1.20 g, 3.23 mmol) and (S)-tert-butyl 3-chloro-2-hydroxypropylcarbamate (1.35 g, 6.47 mmol) in DMF (10 mL), LiOtBu (1.03 g, 12.94 mmol) is added at 0° C. The mixture is stirred at 25° C. for 45 h. The starting material 10 is not consumed completely. Saturated NH4Cl is then added; the organic phase is extracted with EtOAc (2×20 mL), washed with brine solution, dried and concentrated. The crude residue is dissolved in 20 mL of DCM-TFA mixture (8:2) and stirred at 25° C. for 3 h. RM is concentrated and dissolved in water (10 mL), the aqueous layer is washed with diethyl ether (2×50 mL), basified with saturated NaHCO3 and extracted with DCM (2×50 mL). The DCM layer is dried and concentrated. The crude is purified by column chromatography on silica gel using hexane-EtOAc mixtures to obtain the product as an off-white solid (500 mg) in 45% (based on recovery of starting material) over 2 steps.
    • 1H NMR (400 MHz, CDCl3): δ 7.36 (dd, J=14.2 Hz, 2.3 Hz, 1H), 7.09 (dd, J=8.8 Hz, 1.7 Hz, 1H), 6.96 (t, J=9.5 Hz, 1H), 4.72-4.59 (m, 1H), 4.00 (t, J=8.3 Hz, 1H), 3.79 (dd, J=8.7 Hz, 6.8 Hz, 1H), 3.30 (t, J=6.2 Hz, 4H), 3.03 (dq, J=13.6 Hz, 4.2 Hz, 2H), 0.90 (t, J=6.2 Hz, 4H), 0.10 (s, 6H). 13C NMR (100 MHz, CDCl3): δ 155.1 (d, J=244.3 Hz), 154.7, 137.9 (d, J=9.0 Hz), 132.1 (d, J=10.3 Hz), 112.0 (d, J=4.3 Hz), 113.8 (d, J=3.2 Hz), 107.4 (d, J=26.9 Hz), 73.8, 51.0, 47.8, 45.01, 14.4, −2.9. IR (CHCl3): ν 3685, 3021, 2955, 2809, 2401, 1747, 1515, 1416, 1219, 1029, 991, 870, 771, 667 cm−1. M.P: 94-96° C. ESI-MS: 360.11 (M+Na).

Preparation of (S)—N-((3-(4-(4,4-dimethyl-1,4-azasilinan-1-yl)-3-fluorophenyl)-2-oxooxazolidin-5-yl)methy)acetamide (12) (NDS 10024)

  • Figure US20140296133A1-20141002-C00034
  • To solution of amine 11 (300 mg, 0.9 mmol) and DIPEA (0.3 mL, 1.78 mmol) in dry THF (4.0 mL), acetylchloride (0.08 mL, 1.07 mmol) is added at 0° C., and stirred at 25° C. for 3 h. Further, saturated NaHCO3 (5.0 mL) is added to the reaction mixture and extracted with EtOAc (2×5 mL). The organic layer is washed with brine, dried and concentrated. The product is purified by column chromatography on silica gel using hexane-EtOAc mixtures to obtain the product as an off-white solid (170 mg) in 50% yield.
  • 1HNMR (400 MHz, CDCl3): δ 7.33 (d, J=13.8 Hz, 1H), 7.02-6.94 (m, 2H), 6.52 (t, J=5.8 Hz, 1H), 4.77-4.73 (m, 1H), 3.99 (t, J=9.04 Hz, 1H), 3.72 (dd, J=9.0 Hz, 6.8 Hz, 1H), 3.69-3.58 (m, 2H), 3.31 (t, J=5.5 Hz, 4H), 2.01 (s, 3H), 0.89 (t, J=5.5 Hz, 4H), 0.10 (s, 6H). 13C NMR (100 MHz, CDCl3): δ171.2, 155.0 (d, J=244.3 Hz), 154.5, 138.2 (d, J=9.3 Hz), 131.5, 119.9, 114.0 (d, J=3.4 Hz), 107.6 (d, J=27.1 Hz), 71.9, 50.9, 47.7, 41.9, 23.0, 14.3, −2.9. IR (CHCl3): ν 2401, 1759, 1675, 1519, 1216, 759, 669 cm−1 M.P: 123-126° C. ESI-MS: 380.10 (M+H).
SCHEME 1
  • Figure US20140296133A1-20141002-C00015
    Figure US20140296133A1-20141002-C00016

SCHEME2

  • Figure US20140296133A1-20141002-C00018
    Figure US20140296133A1-20141002-C00019

SCHEME 3

  • Figure US20140296133A1-20141002-C00020

SCHEME 4

  • Figure US20140296133A1-20141002-C00021

str1

str1

Dr. D. Srinivasa Reddy of NCL winner Shanti Swarup Bhatnagar Award 2015

see

http://oneorganichemistoneday.blogspot.in/2015/02/dr-d-srinivasa-reddy.html

Dr. Srinivasa Reddy of CSIR-NCL bags the

prestigious Shanti Swarup Bhatnagar Prize

The award comprises a citation, a plaque, a cash prize of Rs 5 lakh

dr

The Shanti Swarup Bhatnagar Prize for the year 2015 in chemical sciences has been awarded to Dr. D. Srinivasa Reddy of CSIR-National Chemical Laboratory (CSIR-NCL), Pune for his outstanding contributions to the area of total synthesis of natural products and medicinal chemistry.
This is a most prestigious award given to the scientists under 45 years of age and who have demonstrated exceptional potential in Science and Technology. The award derives its value from its rich legacy of those who won this award before and added enormous value to Indian Science.
Dr. Reddy will be bestowed with the award at a formal function, which shall be presided over by the honourable Prime Minister. The award, named after the founder director general of Council of Scientific & Industrial Research (CSIR), Dr. Shanti Swarup Bhatnagar, comprises a citation, a plaque, a cash prize of Rs 5 lakh.
Dr. Reddy’s research group current interests are in the field of total synthesis and drug discovery by applying medicinal chemistry. He has also been involved in the synthesis of the agrochemicals like small molecules for crop protection. The total synthesis of more than twenty natural products has been achieved in his lab including a sex pheromone that attracts the mealy bugs and has potential use in the crop protection. On the medicinal chemistry front significant progress has been made by his group using a new concept called “Silicon-switch approach” towards central nervous system drugs. Identification of New Chemical Entities for the potential treatment of diabetes and infectious diseases is being done in collaboration with industry partners.
His efforts are evidenced by 65 publications and 30 patents. He has recently received the NASI-Reliance industries platinum jubilee award-2015 for application oriented innovations and the CRSI bronze medal. In addition, he is also the recipient of Central Drug Research Institute award for excellence in the drug research in chemical sciences and scientist of the year award by the NCL Research Foundation in the year 2013. Dr. Reddy had worked with pharmaceutical companies for seven years before joining CSIR-NCL in 2010.

AN INTRODUCTION

Ph.D., University of Hyderabad, 2000 (Advisor: Professor Goverdhan Mehta).

Post-doctoral with Profs. Sergey A. Kozmin(University of Chicago, USA) and Prof.

Jeffrey Aubé (University of Kansas, USA)

Experienced in leading drug discovery programs (Dr. Reddy’s & TATA Advinus – 7

years of pharma experience)

Acquired skills in designing novel small molecules and lead optimization

Experienced in planning and execution of total synthesis of biologically active

molecules with moderate complexity

One of the molecules is currently in human clinical trials.

MYSELF WITH HIM

s reddy ncl
DEC2014 NCL PUNE INDIA
DR ANTHONY WITH DR REDDY

OTHER AUTHORS

Remya Ramesh

Remya Ramesh

M.Sc Applied Chemistry
Senior Researcher
Seetharamsingh Balamkundu
Pankaj Khairnar
Srikant Viswanadha

Srikant Viswanadha

Ph.D.
Vice President
Incozen Therapeutics Pvt. Ltd. · Drug Discovery

////////

C[Si]1(C)CCN(CC1)c2ccc(cc2F)N3C[C@H](CNC(C)=O)OC3=O

Dr. Ashok Kumar, President – Research and Development (Chemical) at IPCA LABORATORIES LTD


Dr. Ashok Kumar

PRESIDENT – R&D (Chemical) at IPCA LABORATORIES LTD
LINKS
 Intro

The 25-year process patent regime allowed a large number of generic companies in India to reap rich dividends, but there were few who believed in the need to go beyond the horizon of process development to tap into unexplored terrains.

In the year 2000, when Dr Ashok Kumar joined the board of Mumbai-based IPCA Labs, he was determined to implement a different strategy to accelerate IPCA’s R&D initiatives. Having seen IPCA grow from a 350-crore company to one clocking an annual turnover of over 2,500 crore, Dr Ashok Kumar, president- Center for Research and Development, IPCA Labs, is now leaving no stone unturned to exploit the biotech and drug discovery space.

 Dr. Ashok Kumar

Dr Kumar completed his M Sc in Chemistry from Kumaun University, now in Uttarakhand. He then decided to pursue his PhD in organic chemistry and joined Banaras Hindu University (BHU), but opted out three months later to do PhD from the Central Drug Research Institute (CDRI), Lucknow, under the guidance of the then director of the CDRI, Dr Nityanand.

Dr Kumar did his post doctoral studies from the University of Sussex, UK. “During the 1980s, jobs in scientific research were not available in India. It was always good to go for higher studies abroad,” he says about the reason for going abroad. “Dr Nityanand taught me to be explorative and think of new ways to approach a subject. I still follow that process,” he says. In 1984, Dr Kumar decided to return to India and took up a job at the Imperial Chemical Laboratories (ICI), Mumbai. In 1994, he joined Lupin Labs where he was once again involved in process development of small molecules.

In 2000, he joined IPCA Labs where he immediately focused on bringing about two changes – introducing a library and bringing in systems like a nuclear magnetic resonance (NMR), which at that time was the costliest instrument. “I understood the importance of high-end technologies since my PhD years at the CDRI (which housed a couple of NMRs) and then in the UK. You do not enjoy organic chemistry without an NMR. My main objective at IPCA was cost reduction along with process development.”

In the last few years, IPCA’s R&D team has brought out over 100 products. Under Dr Kumar, IPCA has an R&D center in Mumbai and another parallel R&D center in Ratlam, Madhya Pradesh. “In Mumbai, we have around 60 people. The Mumbai team takes care of basic chemistry and small-scale development. Scaling up is done in Ratlam,” he explains. IPCA is also coming up with a facility at Vadodara, Gujarat, that will look into large-scale manufacture of both organic and biotech drugs. The facility will have a strategic importance for the company. “We are growing at a rate of 20 per cent year-on-year and, next year, we intend to add 500 crore to our revenue. For that, we need more products to come to the market and more volume,” he adds.

Apart from organic chemistry, Dr Kumar is currently aligning his attention to two promising but high risk segments – fermentation-based products and biosimilars. “We are working on five-to-six molecules, mainly active metabolites that are intermediates or biotech drugs,” he adds. IPCA has also collaborated with two companies in India for the development of biosimilars. Currently, there are three biosimilar products in the pipeline.

The R&D team at IPCA ventured into drug discovery three years ago. It has two products in the pipeline; one anti-malarial and the other anti-thrombotic. “We will be filing the investigational new drug application for one molecule this year and for the other next year. The success rate here is 99 per cent,” adds Dr Kumar. IPCA has also joined hands with the CDRI and licensed two molecules in the anti-malarial space. One of these molecules is currently in phase-I stage.

Innogen summit India 2016, 18-19 Aug, Mumbai, India, HOTEL HOLIDAY INN, Mumbai International Airport,Organised by Inventicon Business Intelligence Pvt. Ltd………topic is Supergenerics, Innovation in Generics, commercialization, regulatory, other insights,

A0a1

Dr. Ashok Kumar, President – Centre for Research & Development, Ipca Laboratories Ltd, at Innogen summit India 2016, 18-19 Aug, Mumbai, India,, HOTEL HOLIDAY INN, Mumbai International Airport,Organised by Inventicon Business Intelligence Pvt. Ltd — with DR ASHOK KUMAR OF IPCA at Holiday Inn-Mumbai Intl Airport.

 

A2

PANEL DISCUSSION, Dr. Ashok Kumar, President – Centre for Research & Development, Ipca Laboratories Ltd , Dr. Nilima A. Kshirsagar, National Chair Clinical Pharmacology, ICMR Government of India, Yugal Sikri, Chairman – Pharmaceutical Management, School of Business Management, SVKM’s Narsee Monjee Institute of Management Studies — with Yugal Sikri,, Nilima A. Kshirsagarand ASHOK KUMAR OF IPCA at Holiday Inn-Mumbai Intl Airport.

JOURNEY

2005…..PRESIDENT
In 2000, he joined IPCA Labs
1994, he joined Lupin Labs where he was once again involved in process development of small molecules.
1984 Dr Kumar decided to return to India and took up a job at the Imperial Chemical Laboratories (ICI), Mumbai.
Dr Kumar did his post doctoral studies from the University of Sussex, UK.
PhD in organic chemistry and joined Banaras Hindu University (BHU), but opted out three months later to do PhD from the Central Drug Research Institute (CDRI), Lucknow, under the guidance of the then director of the CDRI, Dr Nityanand.
Dr Kumar completed his M Sc in Chemistry from Kumaun University, now in Uttarakhand
 
 DR NITYANAND
 DIRECTOR, CDRI, LUCKNOW, INDIA
img_Inanim01.jpg
img_pgene01.jpg

Experience

PRESIDENT – R&D

IPCA LABORATORIES LTD

2005 – Present (10 years)

Patent 1

chlorthalidone is 3-hydroxy-3-(3′-sulfamyI-4′- chlorophenyl)phtalimidine and is represented by the structural formula shown below.

Figure imgf000002_0001
Figure imgf000004_0001

Chlorthalidone Formula 1

(Scheme 2). The starting material, 2-(4′-chlorobenzoyl) benzoic acid, of Formula (2) and its preparation was reported earlier for example in patents US 4500636, US 30555904, US4379092, US 3764664.

Figure imgf000008_0002
Figure imgf000008_0001

Formula 9 CIS03H

Figure imgf000008_0003
Figure imgf000008_0004

Chlorthalidone Formula 10 Formula 1

Figure imgf000008_0005

 PATENT 2

 https://www.google.co.in/patents/US7847094Quetiapine and its process for preparation is first disclosed in the patent specification EP0240228 and various other processes for the preparation are disclosed in EP0282236, WO0155125, WO9906381, WO2004076431.

Figure US07847094-20101207-C00001

 PATENT 3

http://www.google.com/patents/US20080009635

  . The chemical name of Ondansetron is 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl)-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one and is represented by the structural formula given below:

Figure US20080009635A1-20080110-C00001

PATENT 4

  • scheme 2.
  • Figure US20100081847A1-20100401-C00002
 
 AT A SEMIMAR
Map of ipca

Chemical Research & Development Centre

123-AB, Kandivli Industrial Estate, Kandivli (West)
Mumbai 400 067, Maharashtra

icon_phone.jpg+91 (22) 6647 4755 / 56
icon_fax.jpg+91 (22) 6647 4757
Kumaun University
 Imperial Chemical Laboratories (ICI), Mumbai
/////Dr. Ashok Kumar, PRESIDENT, R&D, IPCA LABORATORIES LTD

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deleted

ORGANIC SPECTROSCOPY INTERNATIONAL HAS 2 LAKH VIEWS


ORGANIC SPECTROSCOPY INTERNATIONAL HAS 2 LAKH VIEWS

Read by one and all in academics and industry

link is ……http://orgspectroscopyint.blogspot.in/

I get minimum 1000 hits in a day and all across the world

 

 

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He was only in first standard in school when I was hit by a deadly one in a million spine stroke called acute transverse mylitis, it made me 90% paralysed and bound to a wheel chair, Now I keep him as my source of inspiration and helping millions, thanks to millions of my readers who keep me going and help me to keep my son happy
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जिंदगी चल जाये।
औकात बस इतनी देना,
कि औरों का भला हो जाये।

 

9-(5-oxotetrahydrofuran-2-yl)nonanoic acid methyl ester


9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester

353
Name 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester
Synonyms
Name in Chemical Abstracts 2-Furannonanoic acid, tetrahydro-5-oxo-, methyl ester
CAS No 22623-86-5
Molecular formula C14H24O4
Molecular mass 256.35
SMILES code O=C1OC(CC1)CCCCCCCCC(=O)OC

1H NMR

1H NMR

1H-NMR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester
500 MHz, CDCl3
delta [ppm] mult. atoms assignment
1.24-1.45 m 10 H 4-H, 5-H, 6-H, 7-H, 8-H
1.57 m 2 H 3-H
1.70 m 1 H 9-H
1.82 m 1 H 9-H
2.27 t 2 H 2-H
2.30 m 2 H 3-H (ring)
2.50 m 2 H 4-H (ring)
3.67 s 3 H O-CH3
4.48 m 1 H 2-H (ring)

NMR XXX

13C NMR

13C NMR

13C-NMR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester
125.7 MHz, CDCl3
delta [ppm] assignment
24.9 C3
25.2 C9
28.0-29.2 C4, C5, C6, C7, C8, C3 (ring)
34.0 C2
35.5 C4 (ring)
51.4 O-CH3
81.0 C2 (ring)
174.2 C1 (O-C(=O)-)
177.2 C5 (O-C(=O)-, ring)
76.5-77.5 CDCl3

13C XXX

IR

IR

IR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester
[Film, T%, cm-1]
[cm-1] assignment
2931, 2856 aliph. C-H valence
1776 C=O valence, lactone
1737 C=O valence, ester
Cu
10-Undecenoic acid methyl esterIodoacetic acid ethyl esterreacts to9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl esterIodoethane

Synthesis of 9-(5-oxotetrahydrofuran-2-yl)nonanoic acid methyl ester

Reaction type: addition to alkenes, radical reaction, ring closure reaction
Substance classes: alkene, halogencarboxylic acid ester, lactone
Techniques: working with cover gas, stirring with magnetic stir bar, heating under reflux, evaporating with rotary evaporator, filtering, recrystallizing, heating with oil bath
Degree of difficulty: Easy

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Operating scheme

Operating schemeInstructions

http://www.oc-praktikum.de/nop/en/instructions/pdf/4005_en.pdf

Instruction (batch scale 100 mmol)

Equipment 250 mL two-neck flask, protective gas supply, reflux condenser, heatable magnetic stirrer, magnetic stir bar, rotary evaporator, Buechner funnel, suction flask, desiccator, oil bath Substances undecenoic acid methyl ester (bp 248 °C) 19.8 g (22.3 mL, 100 mmol) iodoacetic acid ethyl ester (bp 73-74 °C/ 21 hPa) 27.8 g (15.4 mL, 130 mmol) copper powder (finely powdered, >230 mesh ASTM) 30.5 g (480 mmol) tert-butyl methyl ether (bp 55 °C) 130 mL petroleum ether (bp 60-80 °C) 300 mL Reaction In a 250 mL two-neck flask with magnetic stir bar and a reflux condenser connected with a protective gas piping 19.8 g (22.3 mL, 100 mmol) undecenoic acid methyl ester and 27.8 g (15.4 mL, 130 mmol) iodoacetic acid ethyl ester are mixed with 30.5 g (480 mmol) copper powder under a protective gas atmosphere. Afterwards the reaction mixture is stirred at 130 °C oil bath temperature under protective gas for 4 hours. (Reaction monitoring see Analytics.)

Work up The reaction mixture is cooled down to room temperature, 30 mL tert-butyl methyl ether are added, the mixture is stirred for 5 minutes and filtered off. The copper powder on the filter is washed four times with 25 mL tert-butyl methyl ether each. Filtrates and wash solutions are combined, the solvent is evaporated at the rotary evaporator. A yellow oil remains as crude product. Crude yield: 25.4 g.

The crude product is dissolved in 300 mL petroleum ether under reflux. The solution is allowed to cool down to room temperature, then it is stored in the refrigerator over night for complete crystallization. The crystalline product is sucked off over a Buechner funnel and dried in the vacuum desiccator. The mother liquor is stored again in the refrigerator for a check of complete crystallization. Yield: 19.5 g (76.1 mmol, 76%); white solid, mp 34 °C Comments In order to achieve a quantitative reaction within 4 hours, a fivefold excess of copper is used.

Waste management Recycling The copper powder can be used three times.

Waste disposal Waste Disposal evaporated tert-butyl methyl ether (might contain iodoethane) organic solvents, containing halogen mother liquor from recrystallization organic solvents, containing halogen copper powder solid waste, free from mercury, containing heavy metals

Time 6-7 hours

Break After heating and before recrystallizing

Degree of difficulty Easy

Analytics Reaction monitoring with TLC Sample preparation: Using a Pasteur pipette, two drops of the reaction mixture are taken and diluted with 0.5 mL diethyl ether. TLC-conditions: adsorbant: TLC-aluminium foil (silica gel 60) eluent: petroleum ether (60/80) : acetic acid ethyl ester = 7 : 3 visualisation: The TLC-aluminium foil is dipped in 2 N H2SO4 and then dried with a hot air dryer. Reaction monitoring with GC Sample preparation: Using a Pasteur pipette, one drop of the reaction mixture is taken and diluted with 10 mL dichloromethane. From this solution, 0.2 µL are injected. 10 mg from the solid product are dissolved in 10 mL dichloromethane. From this solution, 0.2 µL are injected. GC-conditions: column: DB-1, 28 m, internal diameter 0.32 mm, film 0.25 µm inlet: on-column-injection carrier gas: hydrogen (40 cm/s) oven: 90 °C (5 min), 10 °C/min to 240 °C (40 min) detector: FID, 270 °C Percent concentration was calculated from peak areas.

Chromatogram

crude product chromatogram

GC: crude product
column DB-1, L=28 m, d=0.32 mm, film=0.25 µm
inlet on column injection, 0.2 µL
carrier gas H2, 40 cm/s
oven 90°C (5 min), 10°C/min –> 240°C (40 min)
detector FID, 270°C
integration percent concentration calculated from relative peak area

pure product chromatogram

GC: pure product
column DB-1, L=28 m, d=0.32 mm, film=0.25 µm
inlet on column injection, 0.2 µL
carrier gas H2, 40 cm/s
oven 90°C (5 min), 10°C/min –> 240°C (40 min)
detector FID, 270°C
integration percent concentration calculated from relative peak area

Substances required

Batch scale: 0.01 mol 0.1 mol 10-Undecenoic acid methyl ester
Educts Amount Risk Safety
10-Undecenoic acid methyl ester
19.8 g H- EUH- P-
Iodoacetic acid ethyl ester
GHS06 GHS05 Danger
27.8 g H300 H314 EUH- P264 P280 P305 + 351 + 338 P310
Reagents Amount Risk Safety
Copper powder
GHS09 Warning
30.5 g H400 EUH- P273
Solvents Amount Risk Safety
tert-Butyl methyl ether
GHS02 GHS07 Danger
130 mL H225 H315 P210
Petroleum ether (60-80)
GHS02 GHS08 GHS07 GHS09 Danger
300 mL H225 H304 H315 H336 H411 EUH- P210 P261 P273 P301 + 310 P331
Others Amount Risk Safety
Sulfuric acid 2N
GHS05 Danger
H314 H290 EUH- P280 P301 + 330 + 331 P305 + 351 + 338 P309 + 310
Solvents for analysis Amount Risk Safety
Petroleum ether (60-80)
GHS02 GHS08 GHS07 GHS09 Danger
H225 H304 H315 H336 H411 EUH- P210 P261 P273 P301 + 310 P331
Acetic acid ethyl ester
GHS02 GHS07 Danger
H225 H319 H336 EUH066 P210 P261 P305 + 351 + 338
Dichloromethane
GHS08 GHS07 Warning
H351 H315 H319 H335 H336 H373 P261 P281 P305 + 351 + 338

Substances produced

Batch scale: 0.01 mol 0.1 mol 10-Undecenoic acid methyl ester
Products Amount Risk Safety
9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester

Equipment

Batch scale: 0.01 mol 0.1 mol 10-Undecenoic acid methyl ester
two-necked flask 250 mL two-necked flask 250 mL protective gas piping protective gas piping
reflux condenser reflux condenser heatable magnetic stirrer with magnetic stir bar heatable magnetic stirrer with magnetic stir bar
rotary evaporator rotary evaporator suction filter suction filter
suction flask suction flask exsiccator with drying agent exsiccator with drying agent
oil bath oil bath

Simple evaluation indices

Batch scale: 0.01 mol 0.1 mol 10-Undecenoic acid methyl ester
Atom economy 53.9 %
Yield 76 %
Target product mass 19.5 g
Sum of input masses 370 g
Mass efficiency 53 mg/g
Mass index 19 g input / g product
E factor 18 g waste / g product

………………

………

CARMEN DRAHL….Tribute to a Great Writer


CARMEN DRAHL

Award-winning science communicator and social media power user based in Washington, DC.

Carmen Drahl is a multimedia science journalist and chemistry communicator based in Washington, DC.

A social media evangelist, Carmen started her first chemistry blog in 2006. Today, she regularly leverages Twitter, Facebook, and Google Plus Hangouts in her reporting.

Carmen has written about how life may have originated on Earth, explained how new medications get their names, and covered the ongoing issues plaguing the forensic science community. Her video on the food science behind 3D printed cocktail garnishes won the 2014 Folio Eddie Award for Best Association Video.

Until December 2014, Carmen worked at Chemical & Engineering News magazine. Her work has also been featured at Scientific American’s blog network, SiriusXM’s Doctor Radio, and elsewhere.

Carmen holds a Ph.D. in chemistry from Princeton University.

 

Specialties:
interviewing, science writing, social media, Twitter, Storify, YouTube,
public speaking, hosting, video production, iPhone videography,
non-linear video editing, blogging (WordPress and Blogger), HTML website
coding

We have been reading her for the past several years and a inspiration for many

Carmen Drahl - Science Communicator

Links

FACEBOOK

https://www.facebook.com/carmenwrites

Carmen Drahl (@carmendrahl) | Twitter

www.linkedin.com/in/carmendrahl/en

http://www.ddn-news.com/

http://cenblog.org/the-safety-zone/

Carmen Drahl – Google+

Carmen Drahl

 

Education

Princeton University

Ph.D., Chemistry

2002 – 2007

Ph.D. with Erik J. SorensenShe was on a team that completed the first total synthesis of
abyssomicin C, a molecule found in small quantities in nature that
showed hints of promise as a potential antibiotic. I constructed
molecular probes from abyssomicin for proteomics studies of its
biological activity.

M.A. with George L. McLendon

worked
toward developing a drug conjugate as a potential treatment for cancer. I
synthesized a photosensitizer dye-peptide conjugate for targeting the
cell death pathway called apoptosis.

image

At a reception before the Alumni Day luncheon, President Tilghman (third
from left) congratulated the winners of the University’s highest awards
for students: (from left) Pyne Prize winners Lester Mackey and Alisha
Holland; and Jacobus Fellowship recipients Sarah Pourciau, Egemen
Kolemen and Carmen Drahl. Unable to attend the event was Jacobus Fellowship winner William Slauter. (photo: Denise Applewhite

B.A., Chemistry

1998 – 2002

Graduated
summa cum laude with specialized honors in chemistry. Honors thesis
entitled “Structural, kinetic, and mechanistic studies: the protein
tyrosine phosphatases CD45 and PTP1B”
Activities and Societies: Phi Beta Kappa

  Carmen Drahl, Class of 2002,

 

Experience

Science Journalist

Freelance

January 2014 – Present Washington D.C. Metro Area

Multimedia
science journalist – I deliver clean products on time. Experience in
reporting on chemistry, food science, history of science, drug
development, science education.

Senior Editor, Chemical & Engineering News

American Chemical Society

August 2007 – December 2014 (7 years 5 months)Washington D.C. Metro Area

Reporting:Cover the science of chemistry for C&EN, the American Chemical
Society’s weekly magazine, circulation 160,000. Track new research
findings daily, particularly in forensic science, drug discovery,
organic chemistry, and food science.

Video:

Doubled circulation to C&EN’s YouTube channel in 2013. Scripted, narrated, edited footage.

Managed a core team of 4 and collaborated with other reporters to
produce 30 videos, some reproduced in The Atlantic, Scientific American,
Eater National, The Daily Mail.

Incepted, scripted, and co-hosted
“Speaking of Chemistry”, a monthly web show that summarizes top
chemistry news for the busy scientist.

Social Media:

Developed magazine-wide best practices for YouTube videos and Twitter. Ran staff workshops about Storify, Slashdot, and Reddit.

Hosting/Public Speaking:

Topics include communicating chemistry simply, transitioning from a
Ph.D. to careers in science communication. Moderated discussions on
chemophobia, social media usage in the chemical sciences. On-camera
co-host for web newscasts produced by ACS.

Innovation:

With
C&EN art and web teams, developed first-for-the-magazine features,
including a 90th anniversary commemorative timeline poster, a pullout
guide to top conference speakers, interactive quizzes and database
searches.

Carmen Drahl, senior editor of Chemical and Engineering News,
used her Ph.D. in chemistry as a springboard into the career she
envisioned for herself. Here she shares some advice that helped her make
the decision.

Carmen Drahl made the transition to a writing
career while earning a Ph.D. in chemistry at Princeton University. Born
and raised in New Jersey, she now lives in Washington, D.C., and reports
for Chemical and Engineering News (C&EN). At C&EN
she has written about how new medications get their names, explained
the science behind a controversial hair-straightening product, and
covered the scientific firestorm sparked by an alleged arsenic life
form. Her work has been featured on SiriusXM’s Doctor Radio, Radio New Zealand’s This Way Up, and elsewhere. Her coverage has also been recognized by MIT’s Knight Science Journalism Tracker.

(Open)1 honor or award
Scientific Cocktails: Award-winning video
Scientific Cocktails: Award-winning video
Speaking of Chemistry: All About Tinsel
Speaking of Chemistry: All About Tinsel

Carmen Drahl

Twitter Maven

World Central Kitchen

March 2013 – August 2014 (1 year 6 months)Washington D.C. Metro Area

she was the “voice of Twitter” for World Central Kitchen, the humanitarian
organization founded by renowned Chef José Andrés. Doubled followers to
Twitter account in 2013, developed Twitter strategy for projects and
events. Edited Annual Report, press releases and other communication
materials. Volunteered in person at outreach events.

Contributing Editor, AWIS Magazine

Association of Women in Science

December 2005 – August 2007 (1 year 9 months)

sHE
reported and wrote profiles of prominent women scientists in a range of
fields (molecular biology, physics, geoscience) for the Research
Advances column in AWIS Magazine.

Writer, various publications

Princeton University

April 2005 – May 2007 (2 years 2 months)

She
reported and wrote news for the Princeton University News Office’s
Research Notes, and wrote news and features for the Princeton University
Chemistry Department’s Industrial Affiliates Program Newsletter and
Chemistry Alumni Newsletter.

Honors & Awards

Eddie Digital Award- Best Video (B-to-B)

FOLIO Magazine

December 2014

Porter Ogden Jacobus Fellowship

Princeton University

February 2007

NSF Graduate Research Fellowship

National Science Foundation

2002

Volunteer Experience & Causes

Board Member

Princeton Alumni Weekly Magazine

October 2013

Advisory Committee

American Institute of Physics News and Media Services

October 2013

Member, Graduate Alumni Leadership Council

Princeton University

2009 – 2012 (3 years)

INTERVIEW

Continuing with the tradition from last two years, I will occasionally post interviews with some of the participants of the ScienceOnline2010 conference that was held in the Research Triangle Park, NC back in January. See all the interviews in this series here. You can check out previous years’ interviews as well: 2008 and 2009.Today, I asked Carmen Drahl, Associate Editor for Science/Technology/Education at Chemical & Engineering News (find her as @carmendrahl on Twitter) to answer a few questions.Welcome
to A Blog Around The Clock. Would you, please, tell my readers a little
bit more about yourself? Where are you coming from (both geographically
and philosophically)? What is your (scientific) background?
i-b183f89fe33d3d9f0b308a6cb30d9b5b-Carmen Drahl pic1.JPGIt’s a pleasure and a privilege to be interviewed, Bora.Good
conversations make me happy. School was fun for me (well, maybe not
grad school) and that’s evolved into a desire to always be learning
something new. I enjoy doing nothing as much as I enjoy doing things. On
Mondays, if I’m not too busy, I take hip-hop dance classes.her hometown is Hackettstown, New Jersey. M&M’s are made there. I got a
bachelor’s in chemistry from Drew University and a Ph.D. in chemistry at
Princeton. Scientifically my expertise hovers somewhere around the
interface between organic chemistry and biochemistry. A short while
after defending my dissertation, I moved to Washington DC to write for Chemical & Engineering News, and that’s where I’ve been for almost three years now.When and how did you first discover science blogs?Scandal
led me to science blogs. Seriously. In March 2006 I was still an
organic chemistry grad student. Everyone in my lab was buzzing about a
set of retractions in the Journal of the American Chemical Society
(disclosure: today I work for the American Chemical Society, which
publishes JACS). A rising young organic chemistry star retracted the
papers because work by one of his graduate students couldn’t be
reproduced. It was a big deal and became an even bigger deal as the
inevitable rumors (salacious and otherwise) surfaced. The blogosphere
had the details first. So that’s where Google pointed me and the other
members of my lab when we searched for more information. I learned about
the awesome (but sadly now defunct) blogs Tenderbutton and The Endless
Frontier, by Dylan Stiles and Paul Bracher, both chemistry grad students
like me. I also discovered the solid mix of chemistry and pharma at
Derek Lowe’s In the Pipeline, which is still the first blog I visit every day.Tell us a little more about your career trajectory so far: interesting projects past and present?

i-b7bd4d4568d9689c2daf400303c886c3-Carmen Drahl pic2.JPGBy
the time I discovered science blogs I knew my career goals were
changing. I’d already been lucky enough to audit a science writing
course at Princeton taught by Mike Lemonick from TIME, and thought that
maybe science writing was a good choice for me. After reading chemistry
blogs for a while I realized “Hey, I can do this!” and started my own
blog, She Blinded Me with Science, in July 2006. It was the typical grad student blog, a mix of posts about papers I liked and life in the lab.

At C&E News I’ve contributed to its C&ENtral Science
blog, which premiered in spring 2008. I’ve experimented with a few
different kinds of posts- observations and on-the-street interviews when
I run into something chemistry-related in DC, in-depth posts from
meetings, and video demos of iPod apps. One of my favorite things to do
is toy with new audio/video/etc technology for the blog.

What is taking up the most of your time and passion these days? What are your goals?

In March I just started a new era in my web existence- I’m becoming a pharma blogger. I’m the science voice at The Haystack,
C&E News’s new pharma blog and one of seven new blogs the magazine
launched last month. My co-blogger is the talented Lisa Jarvis, who’s
written about the business side of pharma for ten years and who brings a
solid science background to the table as well. I kicked us off by
liveblogging/livetweeting a popular session at the American Chemical
Society’s meeting in San Francisco where drug companies reveal for the
first time the chemical structures of potential new drugs being tested
in clinical trials. The whole thing synced to FriendFeed as well. Folks
followed the talks from all three venues, which was great. I hope I can
continue doing that sort of thing in the future.

For
this August, I’m co-organizing a mini-symposium at the American
Chemical Society meeting in Boston about the chem/pharma blogosphere and
its impact on research and communication. I’m in the process of
inviting speakers right now. It’s my first time doing anything like this
and part of me is petrified that no one will show up. Tips on
organizing a conference session and how not to stress when doing so are
welcome!

More broadly, I’d love to get more chemistry bloggers to
connect with the community that attends ScienceOnline. I don’t ever want
to become that old (or not-so-old) person who is clueless about
them-thar newfangled whosiwhatsits that the kids are using nowadays.

What aspect of science communication and/or particular use of the Web in science interests you the most?

A
few things come to mind, actually. I’d like to think that the web has
made grad school a helluva lot less isolating for science grad students.
You have the virtual journal clubs like Totally Synthetic, posts like SciCurious’s letter to a grad student, etc.

As
a journalist the web’s capacity to equalize fascinates me. I’m
extremely lucky to have a staff gig as a science writer without having
gone to journalism school or landed a media fellowhip and it’s weird to
think that my old blog might’ve helped my visibility. I didn’t know Ed
Yong’s story until Scio10 but I think he’s a highly talented example of
how the web can open doors.

The web’s equalizing power goes to
readers of science content as well as writers, of course. In the ideal
situation a reader can give a writer instant feedback and you can get a
real conversation going, something that was much harder with the
snail-paced system of letters to the editor and reader surveys. Not that
the conversation is always civil. Most of C&EN’s readers have a
decent amount of scientific training, but the debate that rages whenever
we run an editorial about climate change is as intense as any I’ve
seen.

In cases like that I don’t know that the web gives people a
good representation of what the consensus is. For folks who don’t have
scientific training, how do you ensure that people don’t just go to the
content that already confirms their pre-existing beliefs about autism or
global warming? John Timmer touched on this more eloquently in his interview with you,
and I agree with him that I don’t think we have an answer yet. Though
on a slightly different note, I will mention that I’ve been enjoying the
New York Times’s recent attempts to recapture the spontaneity of
flipping through the newspaper in online browsing, like the Times Skimmer for Google Chrome.

What are some of your favourite science blogs? Have you discovered any cool science blogs by the participants at the Conference?

In addition to the blogs I’ve already mentioned I enjoy Carbon-Based Curiosities, Wired Science, Chemistry Blog, and Terra Sigillata, to name a few of the 50 or so blogs on my feed reader.

I discovered scads of new blogs at Scio10 but I’ll focus on the one that’s become required reading for me these days: Obesity Panacea.
I’d covered obesity drug development for C&EN but I’d never met
Travis Saunders and Peter Janiszewski or heard of their blog until the
conference.

What was the best aspect of ScienceOnline2010 for
you? Is there anything that happened at this Conference – a session,
something someone said or did or wrote – that will change the way you
think about science communication, or something that you will take with
you to your job, blog-reading and blog-writing?

Dave Mungeris
my hero – his blogging 102 session was packed with practical tips that I
brought back to C&EN for incorporating into our blogs, such as the
use of the Disqus plugin for catching conversations on social networks,
getting smart about using stats and surveys, etc. Some of that’s already
happened, and some of the ideas are still in the works.

I came
for the nuts-and-bolts blogging tips but I stayed for the conversations,
especially the ones at the bar after the official program was done for
the night. And the icing on the cake was seeing folks I’d worked with
but never met, like Cameron Neylon and you, Bora, and catching up with
people I hadn’t seen in months, like Jean-Claude Bradley, Aaron Rowe,
Jennifer Ouellette and Nancy Shute.

It was so nice to meet you in person and thank you for the interview. I hope to see you again next January.


Company: GlaxoSmithKline

Meant to treat: tumors with loss-of-function in the tumor suppressor
protein PTEN (phosphatase and tensin homolog)- 2nd most inactivated
tumor suppressor after p53- cancers where this is often the case include
prostate and endometrial

Mode of action: inhibitor of
phosphoinositide 3-kinase-beta (PI3K-beta). Several lines of evidence
suggest that proliferation in certain PTEN-deficient tumor cell lines is
driven primarily by PI3K-beta.

Medicinal chemistry tidbits: The GSK
team seemed boxed in because in 3 out of 4 animals used in preclinical
testing, promising drug candidates had high clearance. It turned out
that a carbonyl group that they thought was critical for interacting
with the back pocket of the PI3K-beta enzyme wasn’t so critical after
all. When they realized they could replace the carbonyl with a variety
of functional groups, GSK2636771 eventually emerged. GSK2636771B (shown)
is the tris salt of GSK2636771.

Status in the pipeline: Phase I clinical trials……….http://cenblog.org/the-haystack/2012/03/liveblogging-first-time-disclosures-from-acssandiego/

CARMEN

Posted By on Mar 24, 2012

Phone: 202-872-4502

Fax: 202-872-8727 or -6381


Company: GlaxoSmithKline

Meant to treat: tumors with loss-of-function in the tumor suppressor
protein PTEN (phosphatase and tensin homolog)- 2nd most inactivated
tumor suppressor after p53- cancers where this is often the case include
prostate and endometrial

Mode of action: inhibitor of
phosphoinositide 3-kinase-beta (PI3K-beta). Several lines of evidence
suggest that proliferation in certain PTEN-deficient tumor cell lines is
driven primarily by PI3K-beta.

Medicinal chemistry tidbits: The GSK
team seemed boxed in because in 3 out of 4 animals used in preclinical
testing, promising drug candidates had high clearance. It turned out
that a carbonyl group that they thought was critical for interacting
with the back pocket of the PI3K-beta enzyme wasn’t so critical after
all. When they realized they could replace the carbonyl with a variety
of functional groups, GSK2636771 eventually emerged. GSK2636771B (shown)
is the tris salt of GSK2636771.

Status in the pipeline: Phase I clinical trials……….http://cenblog.org/the-haystack/2012/03/liveblogging-first-time-disclosures-from-acssandiego/

CARMEN

Posted By on Mar 24, 2012

Phone: 202-872-4502

Fax: 202-872-8727 or -6381

  1. Map of washington dc
Washington, D.C.
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Susan Mayne, Ph.D. Director of FDA’s Center for Food Safety and Applied Nutrition


 

Susan Mayne

Susan Mayne, Ph.D.

Susan Mayne, Ph.D. Director of FDA’s Center for Food Safety and Applied Nutrition

Susan Mayne (@STMYale) | Twitter

www.linkedin.com/pub/susan-mayne/a/881/452/en

http://www.researchgate.net/profile/Susan_Mayne

She is  passionate about food safety and nutrition and their role in public health. I especially enjoy the intersection of science and policy, leading me to recently relocate to the FDA.

Education

ELAM (Executive Leadership for Academic Medicine)

 

 

Experience

Director, Center for Food Safety and Applied Nutrition

FDA

January 2015 – Present College Park, Maryland

C.-E.A. Winslow Professor of Epidemiology

Yale University School of Medicine

1988 – January 2015 (27 years)Yale School of Public Health

Susan T. Mayne joined the U.S. Food and Drug Administration (FDA) as the new director of the Center for Food Safety and Applied Nutrition (CFSAN), replacing her predecessor Michael Landa, who led the center for more than four years.

Susan T. Mayne is C.-E.A. Winslow Professor of Epidemiology with tenure and Chair, Department of Chronic Disease Epidemiology at the Yale School of Public Health.

Dr. Mayne is also Associate Director of the Yale Comprehensive Cancer Center, being responsible for Population Sciences.

She also directs a pre-doctoral training program at Yale in Partnership with the U.S. National Cancer Institute, to train students in modern methodologies for evaluating lifestyle determinants of human cancer risk, with an emphasis on nutritional, environmental, and occupational determinants, including their interactions with genetic factors.

Dr. Mayne earned a Ph.D. in nutritional biochemistry from Cornell University, with minors in biochemistry and toxicology, and a B.A. in chemistry from the University of Colorado.

Dr. Mayne is a fellow of the American College of Epidemiology, and of the Executive Leadership in Academic Medicine (ELAM) Program for Women. She has authored or co-authored over 180 articles/book chapters.

She also has served on several editorial boards including the Journal of Nutrition, Cancer Epidemiology, Biomarkers and Prevention, and Nature Reviews Clinical Oncology.

Dr. Mayne has served on several National Academy of Sciences committees, including most recently the Committee that established Dietary Reference Intakes for Vitamin D and Calcium.

She is currently on the Food and Nutrition Board of the National Academy of Sciences, and recently completed a 5-year term on the Board of Scientific Counselors for the U.S. National Cancer Institute. Her research emphasizes lifestyle determinants of human cancer risk.

Mayne certainly boosts the academic credentials of an Ivy League scholar. CFSAN’s new director has researched the role of food, nutrition and obesity as risks for chronic disease, and she is the author or co-author of more than 200 scientific publications, according to FDA. She received a B.A. in chemistry from the University of Colorado, and went on to earn a Ph.D. in nutritional sciences, with minors in biochemistry and toxicology, from Cornell University.

“While I make no claims as an expert on food safety, I studied toxicology while earning my Ph.D., and have conducted research into relationships between chemical contaminants and cancer risk, as well as studying microbes and their role in human cancer,” Mayne said in the Q&A. “Thus, I think about things from the perspective of both benefits and risks, and am equally interested in both areas.”

Mayne grew up in rural Colorado. She understands agriculture and comes from a health-conscious family. She said her grandmother lived to be one year shy of age 100 and produced most of her food on a farm in rural Pennsylvania. Mayne’s dad had a small ranch in Colorado where he raised cattle. She characterized her 80-something-year-old mom as “the image of successful aging.”

“She chooses healthy foods, is physically active daily, and frequently sends me pictures of her hikes in the Colorado mountains,” Mayne wrote.

Susan Mayne, PhD

C.-E.A. Winslow Professor of Epidemiology (Chronic Diseases)

Susan T. Mayne, Ph.D., an expert in the lifestyle determinants of cancer risk, has been named the C.-E.A. Winslow Professor of Epidemiology at the Yale School of Public Health (YSPH).

Mayne’s research has emphasized the role of dietary factors in the etiology of several major cancers. She also studies other lifestyle factors, such as tobacco and alcohol use, and their interaction with genetics in cancer risk.

Recently, Mayne co-authored a study that found that indoor tanning significantly raises the risk of an increasingly common form of skin cancer in young people. Mayne and colleagues at the School of Public Health reported online in the Journal of the American Academy of Dermatology in December that people under the age of 40 who had tanned indoors had a 69 percent increased risk of early-onset basal cell carcinoma. The team found that the association was strongest among women, and that the risk increased with years of tanning use.

Mayne is head of the Division of Chronic Disease Epidemiology, which includes 28 faculty members. She is also associate director of Yale Cancer Center, where she is responsible for Population Sciences. Mayne, who earned her doctorate from Cornell University, has led Yale’s Cancer Prevention and Control Research Program for 17 years to record-high levels of National Institutes of Health (NIH) funding and productivity. She developed the Yale-National Cancer Institute partnership, which gives faculty and students access to important national cohort studies for research, as well as an NIH-funded training program in cancer epidemiology and genetics, now entering its ninth year. She has received the Distinguished Teaching Award at YSPH.

A member of several editorial boards, Mayne is a fellow of the American College of Epidemiology and of the Executive Leadership in Academic Medicine Program for Women. She has authored or co-authored over 170 articles and book chapters.

The C.-E.A. Winslow Memorial Fund was established in 1958 by an anonymous donor to support the work of a professor in the Department of Public Health (a precursor to YSPH). It recognizes Charles-Edward Amory Winslow, M.S., Dr.Ph., who served as chair of the department from its founding in 1915 until his retirement in 1945. A scholar with an international reputation and a firm belief in the philosophy of disease prevention, Winslow profoundly influenced both Yale’s department and the burgeoning field of public health.

From the New CFSAN Director: Reflections on My First Two Months

By: Susan Mayne, Ph.D.

I have been the director of FDA’s Center for Food Safety and Applied Nutrition (CFSAN) for two months now. What I have enjoyed the most about this new job has been getting to know the people in CFSAN, who come from incredibly varied and interesting backgrounds. I am truly impressed by their commitment to excellence and dedication to our mission to protect and promote public health.


I have also been struck by the depth and breadth of expertise involved in every initiative CFSAN undertakes. So many scientific disciplines are involved: We rely on the insights of our medical officers, toxicologists, epidemiologists, biologists, chemists, behavioral scientists, and nutritionists. Working with our scientists are our policy and communications experts, economists and lawyers. We all have the same goal: to give the safety of food and cosmetics and nutrition issues the thorough and careful consideration they deserve.

We stand on two legs: strong science and our ability to create policy and regulatory solutions to address public health concerns. The scientific fields in which we work, from genomics to toxicology, are advancing rapidly. The use of new technologies can make our science better and help us to get the information we need more quickly. Yet the constant evolution and adoption of new scientific methods can also pose unique challenges — for example, in interpreting trends in food safety and foodborne illness.

When considering the science of food and cosmetic safety, we assess the scientific certainty, severity, and likelihood of any given risk, and identify those people who would be most vulnerable. We consider what additional research can be undertaken to better clarify the science for decision-making, and use what we currently understand to determine whether the risk can be avoided.

For each issue, we need to examine the full range of options, ranging from consumer education to regulation to enforcement. For regulatory options we work with our legal teams to consider what is possible within our authorities. What are we empowered to do and how does our work intersect with that of other federal agencies? If we take an action, what is the international context, and are there foreign trade implications? What are the views of groups that will be most affected by our decisions, on both the consumer and industry sides? What are the costs and benefits? Have we thoughtfully considered how to ensure high levels of compliance?

I have observed with a great sense of satisfaction how we work together with other federal partners. For example, leaders from the Centers for Disease Control and Prevention (CDC) visited our center recently to share information and discuss how we can best support each other in our joint commitment to food safety. In the brief time I have been here, I have also observed interactions with the U.S. Department of Agriculture, the National Institutes of Health, and the Environmental Protection Agency.

CFSAN’s work is funded by taxpayers and affects people’s lives every day. Our work has real consequences for consumers, businesses, and industry. I have learned the importance of engaging in meaningful conversations with those outside of government, who are affected by our decisions. As we talk to our industry stakeholders, we benefit from their expertise and better understand the real-world constraints they face, and that ultimately helps us to put forth more effective policy. Similarly, we value hearing the perspectives of consumers, medical groups, and the scientific community, which often highlight areas where additional FDA focus is needed to protect public health. In our communications, we strive to accurately convey the risks and/or benefits of any food or product, and to rapidly communicate any emerging health concerns.

I have observed an amazing array of public health issues coming across my desk at CFSAN over the past two months. I am energized by the diverse breadth and depth of activity, and look forward to the challenges and opportunities ahead, and to sharing my thoughts and experiences with you on Twitter and in future blog posts.

Susan Mayne is the Director of FDA’s Center for Food Safety and Applied Nutrition

– See more at: http://blogs.fda.gov/fdavoice/#sthash.gt9fjQow.dpuf

http://blogs.fda.gov/fdavoice/

 

From left to right: Avery LaChance, Leah Ferrucci, Lisa Davis, Susan Mayne

 

 

College Park (Maryland)

 

 

 

University of Maryland, College Park

 

 

 

    1. Map of college park maryland

Simple and effective method for two-step synthesis of 2-(1,3-dithian-2-ylidene)-acetonitrile


Simple and effective method for two-step synthesis of 2-(1,3-dithian-2-ylidene)-acetonitrile (75% overall yield) and molecular modeling calculation of the mechanism by B3LYP and the 6-311++G(2df,2p) basis set.

http://dx.doi.org/10.5935/0100-4042.20140308

Publicado online: dezembro 12, 2014

Método alternativo para a síntese e mecanismo de 2-(1,3-ditiano-2-ilideno)-acetonitrila

Marcelle S. Ferreira; José D. Figueroa-Villar*

Quim. Nova, Vol. 38, No. 2, 233-236, 2015

Artigo http://dx.doi.org/10.5935/0100-4042.20140308

*e-mail: jdfv2009@gmail.com

MÉTODO ALTERNATIVO PARA A SÍNTESE E MECANISMO DE 2-(1,3-DITIANO-2-ILIDENO)-ACETONITRILA

Marcelle S. Ferreira e José D. Figueroa-Villar* Departamento de Química, Instituto Militar de Engenharia, Praça General Tiburcio 80, 22290-270

Rio de Janeiro – RJ, Brasil

Recebido em 18/08/2014; aceito em 15/10/2014; publicado na web em 12/12/2014

ALTERNATIVE METHOD FOR SYNTHESIS AND MECHANISM OF 2-(1,3-DITHIAN-2-YLIDENE)-ACETONITRILE. We report an alternative method for the synthesis of 2-(1,3-dithian-2-ylidene)-acetonitrile using 3-(4-chlorophenyl)-3-oxopropanenitrile and carbon disulfide as starting materials. The methanolysis of the intermediate 3-(4-chlorophenyl)-2-(1,3-dithian-2-ylidene)-3- oxopropanenitrile occurs via three possible intermediates, leading to the formation of the product at a 75% overall yield. Molecular modeling simulation of the reaction pathway using B3LYP 6-311G++(2df,2p) justified the proposed reaction mechanism. Keywords: 2-(1,3-dithian-2-ylidene)-acetonitrile; reaction mechanism; methanolysis; molecular modeling.

3-(4-clorofenil)-2-(1,3-ditiano-2-ilideno)-3-oxopropanonitrila (3): Cristal amarelo. Rendimento: 95%, 2,80 g, pf 158-160 °C, lit.21 159-160 °C;

IV (KBr, cm-1): 2198 (CN), 1612 (C=O), 1585, 1560 (aromático), 678 cm -1 (C-S);

1H RMN (300 MHz, CDCl3) δ 2,38 (m, J 6,9, 2H, CH2); 3,01 (t, J 6,6, 2H, SCH2); 3,17 (t, J 7,2 , 2H, SCH2); 7,43 (d, J 8,5, 2H); 7,83 (d, J 8,5, 2H);

13C RMN (75 MHz, CDCl3) δ 23,9 (CH2), 30,4 (SCH2), 104,2 (CCO), 117,5 (CN), 128,9, 130,5, 135,6, 139,2 (aromático), 185,2 (C=CS), 185,4 (CO).

21…….Rudorf, W. D.; Augustin, M.; Phosphorus Sulfur Relat. Elem. 1981, 9, 329.

…………………………………….

Síntese da 2-(1,3-ditiano-2-ilideno)-acetonitrila (1) Em um balão de fundo redondo de 100 mL foram adicionados 0,400 g (1,4 mmol) de 3-(4-clorofenil)-2-(1,3-ditiano-2-ilideno)-3- -oxopropanonitrila (2) dissolvidos em 15 mL de THF seco, 0,140 g (20 mmol) de sódio e 15 mL de metanol seco sob atmosfera de nitrogênio. A mistura reacional foi mantida sob agitação à 25 °C por 48 h. Em seguida, a mistura reacional foi dissolvida em 30 mL de água destilada e extraída com acetato de etila (3 x 20 mL). A fase orgânica foi seca em sulfato de sódio anidro, filtrada e concentrada a vácuo para se obter o produto bruto, que foi purificado por cromatografia em coluna (silica gel e hexano:acetato de etila 7:3).

2-(1,3-ditiano-2-ilideno)-acetonitrila (1): Cristal branco. Rendimento: 75%, 165 mg, pf. 60-63 °C, lit1 60-62 °C;

1 H RMN (300 MHz, CDCl3) δ 2,23 (m, J 6,8, 2H, CH2); 3,01 (t, J 7,5, 2H, SCH2); 3,06 (t, J 6,9, 2H, SCH2), 5,39 (s, 1H, CH);

13C RMN (75 MHz, CDCl3) δ 22,9 (CH2), 28,7 (SCH2), 28,8 (SCH2), 90,4 (CHCN), 116,3 (CN), 163,8 (C=CS).

1………Yin, Y.; Zangh, Q.; Liu, Q.; Liu, Y.; Sun, S.; Synth. Commun. 2007, 37, 703.

 Acetonitrile, 1,3-dithian-2-ylidene-

CAS 113998-04-2

  • C6 H7 N S2
  • Acetonitrile, 2-​(1,​3-​dithian-​2-​ylidene)​-
  • 157.26
Melting Point 60-62 °C

1H  NMR  predict

2-(1,3-dithian-2-ylidene)-acetonitrile

BR 1H

BR 1H 1

ACTUAL 1H NMR VALUES

1 H RMN (300 MHz, CDCl3)

δ 2,23 (m, J 6,8, 2H, CH2);

3,01 (t, J 7,5, 2H, SCH2);

3,06 (t, J 6,9, 2H, SCH2),

5,39 (s, 1H, CH);

……………………..

13C NMR PREDICT

BR 13C

BR 13C 1

ACTUAL 13C NMR VALUE

13C RMN (75 MHz, CDCl3)

δ 22,9 (CH2),

28,7 (SCH2),

28,8 (SCH2),

90,4 (CHCN),

116,3 (CN),

163,8 (C=CS)

COSY NMR PREDICT

COSY NMR prediction (6)

SYNTHESIS

  Displaying image020.png

Displaying image016.png

Displaying image018.png

Displaying image019.png

Displaying image021.png

2-(1,3-ditiano-2-ilideno)-acetonitrila (1): Cristal branco. Rendimento: 75%, 165 mg, pf. 60-63 °C, lit1 60-62 °C;

1 H RMN (300 MHz, CDCl3) δ 2,23 (m, J 6,8, 2H, CH2); 3,01 (t, J 7,5, 2H, SCH2); 3,06 (t, J 6,9, 2H, SCH2), 5,39 (s, 1H, CH);

13C RMN (75 MHz, CDCl3) δ 22,9 (CH2), 28,7 (SCH2), 28,8 (SCH2), 90,4 (CHCN), 116,3 (CN), 163,8 (C=CS).

WILL BE UPDATED WATCH OUT…………………

Departamento de Química, Instituto Militar de Engenharia, Praça General Tiburcio

Instituto Militar de Engenharia, Rio de Janeiro. BELOW

Entrada do antigo Instituto de Química da UFRGS, um prédio histórico

Equipe – Os módulos foram fabricados na Unisanta sob a supervisão do professor Luiz Renato Lia, coordenador do Curso de Engenharia Química, …

Instituto de Florestas da Universidade Federal Rural do Rio de Janeiro

Praça General Tibúrcio

Praça General Tibúrcio com o Morro da Urca ao fundo

P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.

P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.

P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.

Piecing together the puzzle: understanding a mild, metal free reduction method for large scale synthesis of hydrazines


ORGANIC CHEMISTRY SELECT

Piecing together the puzzle: understanding a mild, metal free reduction method for large scale synthesis of hydrazines

D.L. Browne,* I.R. Baxendale, S.V. Ley, Tetrahedron2011, 67, 10296-10303.

http://www.sciencedirect.com/science/article/pii/S0040402011015304

Full-size image (13 K)

A key intermediate for the synthesis of hydrazines via a mild, metal free reduction of diazonium salts has been isolated and characterized by X-ray analysis. The presence of this intermediate is general, as demonstrated by the preparation of a number of analogues. A discussion of the mechanism and potential benefits of such a process are also described.

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