Dimethylsulfamoyl chloride

Attempts to prepare aulfonyl cyanides from the corresponding sulfonyl chlorides according to the procedure described were unsuccessful when applied to mono-, di-, and trichloromethaneaulfonyl chloride, to dimethylsulfamoyl chloride, and to ethylene- and 2,4-diiiitrophenylsulfonyl chloride. 

Al,(V-dimethylsulfamoyl chloride (4.3 g, 30 mmol) and imidazole (4.1 g, 60 mmol) in chloroform (50 ml) are allowed to react at 25°C (30 min). The mixture is then taken up in water and extracted with benzene, lire organic layer is washed with water, dried and evaporated to a colourless liquid, which is distilled to give a solid (3.3 g, 63%), bo.e 83-87°C, m.p. 45-48°C. 

Aryl sulfonamides can be found in a range of biologically important molecules. Such compounds are generally synthesized from the parent arene in a two-step process of chlorosulfonyla-tion with CISO3H and then reaction with an amine. In a one-step process, indium(III) triflate was found to be the only efficient catalyst for the formation of AfA -dialkylsulfonamides from the reaction of an arene with a dialkylsulfamoyl chloride. As illustrated, the catalytic reaction of dimethylsulfamoyl chloride with toluene in refluxing dichloroethane afforded the sulfonamide product in good yields (eq 6). 

---