Sodium Azide → 2,4,6-Triisopropylbenzenesulfonyl azide

반응식

[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16](Cl)(=[O:18])=[O:17])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CC(C)=O.C(O)C.O>[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([N:20]=[N+:21]=[N-:22])(=[O:18])=[O:17])([CH3:3])[CH3:2]

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실험 절차

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.).