Hydrochloric Acid → 3-(Hydroxymethyl)-N-isopropylbenzenesulfonamide

Participants

Reaction Steps

Sodium hydride (60% oil dispersion, 0.177 g) was added to 3-hydroxymethylbenzenesulfonamide (0.77 g) with stirring in DMF (15 ml) under nitrogen at 21°. After 10 min, isopropyl iodide (0.45 ml) was added followed by a further 0.3 ml after 1 h. After an additional 2 h more isopropyl iodide (0.2 ml) was added. After 3 days more sodium hydride oil dispersion (0.08 g) was added. After another day, the solution was poured into water acidified with 2M hydrochloric acid and the product was extracted with ethyl acetate twice. The combined extracts were washed with brine and evaporated to an oil. This oil was loaded onto a column of silica gel (60 g) and the column was eluted successively with 30%, 50% and 70% ethyl acetate in 40-60 petroleum ether to give the title compound (0.527 g) LCMS RT=2.22 min.

Provenance & Evidence