Sodium hydride → 4-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamide

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Reaction Steps

Sodium hydride (55% in oil, 0.31 g) was added to a stirred solution of 4-bromo-1H imidazole (1.02 g) in dry tetrahydrofuran (20 mL) at room temperature under N2. After 10 minutes, dimethylsulfamoyl chloride (0.81 mL) was added. After stirring for 5 hours, the mixture was diluted with saturated aqueous ammonium chloride (20 mL) and extracted with ethyl acetate (20 mL). The extract was dried over Na2SO4, filtered and concentrated. The white solid was rinsed with diethyl ether and dried to give 1-(dimethylaminosulfonyl)-4-bromoimidazole (1.53 g, 87%). MS (ES+) 256, 254 ([MH]+).

Provenance & Evidence