2-BENZOTHIAZOLESULFONAMIDE, 6-NITRO- → Aminozolamide

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Reaction Steps

The title compound is prepared by first converting 2-mercaptobenzothiazole to 6-nitro-2-benzothiazolesulfonamide and then reducing to the 6-amino analog. 2-Mercaptobenzothiazole was converted to 2,2'-bis-benzothiazole disulfide in 90% yield: m.p. 175-177° C. Nitration in concentrated sulfuric acid gave 6-nitro-2-mercaptobenzothiazole in 59%. m.p. 255-258° C. The sulfenamide was formed by reaction with aqueous sodium hydroxide and sodium hypochlorite and oxidized in the next step without further purification. The oxidation was accomplished by dissolving the sulfenamide in dimethoxyethane, cooling the solution to -5° C., adding the m-chloroperoxybenzoic acid in dimethoxyethane and working up the reaction in the standard manner to obtain a 70% yield: m.p. 179-180°; MS, m/e 259 (M, calcd. 259). Anal. (C7H5N3O4S2) CHN.

Provenance & Evidence