Acetone → 2,4,6-Triisopropylbenzenesulfonyl azide

Participants

Reaction Steps

To a stirred solution of 2,4,6-triisopropylbenzenesulfonyl chloride (18.2 g, 60.0 mmol) in reagent acetone (70 mL) is added a solution of sodium azide (4.3 g, 60 μmol) in ethanol-H2O 1:1 (40 mL). The temperature of the mixture rises from 21° C. to 29° C. during the addition. After stirring at room temperature for 2 hours, the reaction mixture is partitioned between dichloromethane and half saturated brine. The aqueous solution is extracted with dichloromethane (3X), the combined organic solution is washed with half saturated brine, and dried (magnesium sulfate). Removal of solvent in vacuo gives a colorless oil which is purified by flash chromatography (silica gel, hexane-ethyl acetate/4:l) to yield the title compound as a white solid, 18.5 g; mp 44°-44.5° C. (Evans, D. , et al, Journal of the American Chemical Society 112:4011 (1990); mp 43°-44° C.).

Provenance & Evidence