Hydrochloric Acid → (2-Sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate

Participants

Reaction Steps

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g, 0.01 mole), triethylamine (1.4 ml) and 4-dimethylaminopyridine (200 mg) in dimethylformamide (20 ml) was added dimethylsulfamoyl chloride (1.1 ml). The reaction mixture was heated on a steam bath for 18 hours, poured into ice water and excess hydrochloric acid, extracted into ethyl acetate, washed with water and dried over magnesium sulfate. The ethyl acetate was evaporated and the (2-sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate purified by chromatography on a 2 mm preparative silica gel TLC plate developed with chloroform/methanol 9:1 (v/v) m.p.=162°-164° C.

Provenance & Evidence