Development and a Practical Synthesis of Nepafenac Intermediate via Modified Gassman Reaction

Author(s): Marcin Cybulski, Adam Formela, Mariola Mucha, Karolina Klos, Jacek Roszczynski, Jerzy Winiarski

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 7 , 2012


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Abstract:

Modification of nepafenac intermediate synthesis (5A) via Gassman specific ortho-substitution is reported. According to the process, 2-aminobenzophenone (1A) and 2-(methylthio)acetamide (2) were reacted in the convenient temperature conditions, in the presence of N-chlorophthalimide (3) or 1,3-dichloro-5,5-dimethylhydantoin (4), to activate the formation of azasulfonium salt and rearrangement thereof to pure 2-amino-3-benzoyl-α-(methylthio)phenylacetamide (5A). The procedure appears to be suitable for a reaction carried out in a large scale.

Keywords: Gasmann reaction, Nepafenac, N-chlorophthalimide, Sommelet-Hauser-type rearrangement, N-chloroaniline, 2-(methylthio)acetamide, chlorosulfonium, salt, sulfoxide, oxalyl

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Article Details

VOLUME: 9
ISSUE: 7
Year: 2012
Published on: 29 July, 2012
Page: [461 - 464]
Pages: 4
DOI: 10.2174/157017812802139582
Price: $65

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