Acetone → 2,4,6-Triisopropylbenzenesulfonyl azide

HRID 1769561Notes

Reaction equation

HRID 1769561 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+]>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:24]=[N+:25]=[N-:26])(=[O:18])=[O:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chloride

Product 1

HCID 3717072,4,6-Triisopropylbenzenesulfonyl azide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

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.).

Workup

  1. additionThe temperature of the mixture rises from 21° C. to 29° C. during the addition
  2. customthe reaction mixture is partitioned between dichloromethane and half saturated brine
  3. extractionThe aqueous solution is extracted with dichloromethane (3X)
  4. washthe combined organic solution is washed with half saturated brine
  5. dry with materialdried (magnesium sulfate)
  6. customRemoval of solvent in vacuo
  7. customgives a colorless oil which
  8. customis purified by flash chromatography (silica gel, hexane-ethyl acetate/4:l)

Sources & evidence

ORD record
ord-90432235f6ca47c2af4daaa6dac19a96
Source dataset
uspto-grants-1995_01
Patent number
US05380925

Reaction notes

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