Ammonia → 1,2-Benzisothiazole, 5-nitro-

Participants

Reaction Steps

Angewandte Chemie, 36 (1923), 159, and Berichte der deutschen Chemischen Gesellschaft, 58 (1925), 2,095, disclose the reaction of thionaphthene-2,3-dione with ammonia and hydrogen peroxide to give 3-carbamyl-1,2-benzisothiazole and the conversion of the latter to 1,2-benzisothiazole by hydrolysis and decarboxylation. Berichte der deutschen Chemischen Gesellschaft, 56 (1923), 1,630, and Liebigs Annalen der Chemie, 454 (1927), 264, disclose the reaction of 2-formyl-4-nitrophenylsulfenyl bromide with ammonia to give 5-nitro-1,2-benzisothiazole. Benzisothiazoles can also be synthesized by cyclizing o-mercapto-phenyl-carbonyl compounds in the presence of polyphosphoric acid (Annali di Chimica, 53 (1963), No. 5, 577-587). German Laid-Open Application DOS No. 1,670,196 discloses the reaction of dihalomethylaryl compounds with ammonia and sulfur to give benzisothiazoles.

Provenance & Evidence