Acetone → 2,4,6-Triisopropylbenzenesulfonyl azide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2,4,6-triisopropylbenzenesulfonyl chloride (5.0 g, 16.5 mmol, Aldrich, 97%) in reagent grade acetone (20 mL), initially at 17° C., is added a solution of sodium azide (1.18 g, 18.2 mmol) in water (5 mL) and ethanol (5 mL). The mixture is warmed to 27° C. during the addition. After 2 hours, the reaction is partitioned between dichloromethane and brine. The aqueous solution is extracted with dichloromethane (3×). The combined organic extracts are dried (magnesium sulfate) and concentrated in vacuo. The colorless oil is purified by flash chromatography (silica gel, hexane-dichloromethane, 4:1) to afford the title compound as a white solid, 4.93 g; mp 44°-44.5° C. (Evans, D. A., et. al., Journal of the American Chemical Society 112:4011-4030 (1990); mp 43°-44° C.).

Provenance & Evidence