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

반응식

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.C(C1C=C([N+:18]([O-:20])=[O:19])C=CC=1SBr)=O.N>>[N+:18]([C:8]1[CH:7]=[CH:6][C:5]2[S:1][N:2]=[CH:3][C:4]=2[CH:9]=1)([O-:20])=[O:19]

참가 물질

반응물 3

HCID 222Ammonia

HCID 9225Benzisothiazole

HCID 23453962HCID 23453962, 화합물

생성물 1

HCID 1984101,2-Benzisothiazole, 5-nitro-

실험 절차

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.