Benzenesulfonylazide

Tetrahedron Letters, 25, p. 4651, 1984 DOI: 10.1016/S0040-4039(01)91224-9

Benzenesulfonylazide is prepared by the reaction of Benzenesulfonyl Chloride with excess Sodium Azide in a water-ethanol mixture. The formation of ethyl benzenesulfonate as a byproduct may be avoided by addition of neat benzenesulfonyl chloride to an ethanolic solution of sodium azide. A preparation of benzenesulfonyl azide by oxidation of phenylsulfonylhydrazine in the presence of clay-supported iron(III) nitrate (clayfen) has been reported.

Crude benzenesulfonyl azide when heated detonates violently. Use in a fume hood.

recrystallization from ethanol.