Ammonia → 2,1,3-benzoxadiazole-4-sulfonamide

Participants

Reaction Steps

To a stirred solution of 3.0 g of 2,1,3-benzoxadiazole-4-sulfonyl chloride and 200 mL of tetrahydrofuran at -30° C. was added 10 mL of ammonia under an inert atmosphere. The resulting suspension was stirred at ambient temperature for 3 hours. Concentrated ammonium hydroxide (20 mL) and water (20 mL) were added. The reaction was extracted with ethyl acetate and the organic extracts were combined, dried over magnesium sulfate, filtered, and stripped to give a crude solid. Recrystallization from chlorobutanethanol afforded 1.82 g of the title compound as an orange-tan solid, m.p. 157°-159° C.

Provenance & Evidence