Sodium Azide → 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 reagen 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 (3×), 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/4:1) 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