Development and a Practical Synthesis of Nepafenac Intermediate via Modified Gassman Reaction
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: 2-(methylthio)acetamide; Gasmann reaction; N-chloroaniline; N-chlorophthalimide; Nepafenac; Sommelet-Hauser-type rearrangement; chlorosulfonium; oxalyl; salt; sulfoxide
Document Type: Research Article
Publication date: 01 September 2012
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