GB609722A - Improvements in or relating to the preparation of esters of beta-benzyl mercaptovaline, and derivatives and intermediates thereof - Google Patents

Improvements in or relating to the preparation of esters of beta-benzyl mercaptovaline, and derivatives and intermediates thereof

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Publication number
GB609722A
GB609722A GB17553/45A GB1755345A GB609722A GB 609722 A GB609722 A GB 609722A GB 17553/45 A GB17553/45 A GB 17553/45A GB 1755345 A GB1755345 A GB 1755345A GB 609722 A GB609722 A GB 609722A
Authority
GB
United Kingdom
Prior art keywords
benzyl
acid
mercaptovaline
beta
esters
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB17553/45A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB609722A publication Critical patent/GB609722A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Esters of alpha-nitro-beta-benzyl mercapto isovaleric acid, which may be produced by reacting an ester of alpha-nitro-dimethyl acrylic acid with benzyl mercaptan, are reduced in acid solution at a temperature not exceeding 50 DEG C. to yield the corresponding esters of betabenzyl mercaptovaline. The free acid, betabenzyl mercaptovaline, is prepared from its esters by hydrolysis. The reduction is preferably effected by treating the compounds with a metal and acid in a solvent, e.g. with tin and dry hydrogen chloride in anhydrous methanol. Zinc and acids such as acetic acid or other solvents such as glacial acetic acid may also be used. In examples: (1) benzyl mercaptan is slowly added to ethyl alpha-nitrodimethyl acrylate so as to maintain the temperature at about 50 DEG C. The crude product, ethyl alpha-nitro-beta-benzyl mercapto isovalerate is then reduced with tin and dry HCl in methanol at a temperature not exceeding 50 DEG C. The complex tin salt is removed and dissolved in methanol, sodium bicarbonate being then added to a pH of 6 to 7. This solution is treated with hydrogen sulphide to remove all the tin and the residue after evaporating the filtrate is dissolved in methanol to remove sodium chloride. The filtrate is evaporated to obtain beta-benzyl-mercaptovaline ethyl ester hydrochloride; (2) the product of example (1) is refluxed with hydrochloric acid and beta-benzyl mercaptovaline is precipitated by adjusting the solution to a pH of 6 with sodium hydroxide.
GB17553/45A 1944-07-17 1945-07-10 Improvements in or relating to the preparation of esters of beta-benzyl mercaptovaline, and derivatives and intermediates thereof Expired GB609722A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US609722XA 1944-07-17 1944-07-17

Publications (1)

Publication Number Publication Date
GB609722A true GB609722A (en) 1948-10-06

Family

ID=22032875

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17553/45A Expired GB609722A (en) 1944-07-17 1945-07-10 Improvements in or relating to the preparation of esters of beta-benzyl mercaptovaline, and derivatives and intermediates thereof

Country Status (1)

Country Link
GB (1) GB609722A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7105606B2 (en) 2002-10-17 2006-09-12 Lanxess Inc. Polymer blends comprising low molecular weight nitrile rubber

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7105606B2 (en) 2002-10-17 2006-09-12 Lanxess Inc. Polymer blends comprising low molecular weight nitrile rubber

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