Sodium Azide → HCID 14390577, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-acetylbenzo[b]thiophene-2-sulfonamide (5.1 g, 0.02 mole) in glacial acetic acid (50 ml) and concentrated H2SO4 (20 ml) was stirred and heated to 65° C. Sodium azide (5.0 g, 0.077 mole) was added in portions over a 1 hour period. After heating the mixture at 80° C. for another 3 hours, it was poured into a stirred, saturated NaOAc solution (500 ml) cooled in an ice bath. The resulting mixture was refrigerated overnight. The solid was collected, resuspended in water (300 ml), and recollected to obtain 5.25 g (97%) of crude product, m.p. 214°-217° C. Recrystallizations from CH3OH with charcoal decolorization and from CH3CN afforded 1.5 g of 6-acetamido-2-sulfamoylbenzo[b]thiophene, m.p. 231°-232.5° C.

Provenance & Evidence