Acetone → 2,4,6-Triisopropylbenzenesulfonyl azide

HRID 1614699Notes

Reaction equation

[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].CC(C)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>O.C(O)C>[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:24]=[N+:25]=[N-:26])(=[O:18])=[O:17])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 27 °C

Procedure

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.).

Workup

customthe reaction is partitioned between dichloromethane and brine
extractionThe aqueous solution is extracted with dichloromethane (3×)
dry with materialThe combined organic extracts are dried (magnesium sulfate)
concentrationconcentrated in vacuo
customThe colorless oil is purified by flash chromatography (silica gel, hexane-dichloromethane, 4:1)

Sources & evidence

ORD record: ord-1a01264462d44fc6b400565941a41a07
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198548

Reaction notes

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