Palladium-catalyzed amination with benzophenone imine as a new, safe and practical alternative to nitration for the synthesis of 7-amino-2,1,3-benzothiadiazoles

✍ Scribed by Yugang Liu; Mahavir Prashad; Oljan Repič; Thomas J. Blacklock

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 31 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400425

✦ Synopsis

Abstract

Palladium‐catalyzed amination of 7‐bromo‐4‐methyl‐2,1,3‐benzothiadiazole (7) with benzophenone imine as an ammonia equivalent is described as a new, safe and practical alternative to nitration for the synthesis of 7‐amino‐4‐methyl‐2,1,3‐benzothiadiazole (1) in high yield. This methodology was successfully scaled‐up in the pilot plant on 14.0‐kg scale of 7 and was also utilized for the synthesis of 7‐amino‐4,6‐dimethyl‐2,1,3‐ben‐zothiadiazole (12) by the amination of 7‐bromo‐4,6‐dimethyl‐2,1,3‐benzothiadiazole (10).