Ammonia → 1,2-Benzisothiazole, 5-nitro-
Reaction equation
[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]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-042fa446dafa4f2eb93610966eadb656
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04140692
Reaction notes
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