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
Letters in Organic Chemistry
Title:Development and a Practical Synthesis of Nepafenac Intermediate via Modified Gassman Reaction
Volume: 9 Issue: 7
Author(s): Marcin Cybulski, Adam Formela, Mariola Mucha, Karolina Klos, Jacek Roszczynski and Jerzy Winiarski
Affiliation:
Keywords: Gasmann reaction, Nepafenac, N-chlorophthalimide, Sommelet-Hauser-type rearrangement, N-chloroaniline, 2-(methylthio)acetamide, chlorosulfonium, salt, sulfoxide, oxalyl
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.
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Cybulski Marcin, Formela Adam, Mucha Mariola, Klos Karolina, Roszczynski Jacek and Winiarski Jerzy, Development and a Practical Synthesis of Nepafenac Intermediate via Modified Gassman Reaction, Letters in Organic Chemistry 2012; 9 (7) . https://dx.doi.org/10.2174/157017812802139582
DOI https://dx.doi.org/10.2174/157017812802139582 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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