tert-Butanol → N-boc-4-chlorobenzenesulfonamide

HRID 465621Notes

Reaction equation

HRID 465621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:14]([OH:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:9])=[O:10])=[O:13])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 1385874-Chlorobenzenesulfonyl isocyanate

Product 1

HCID 14796817N-boc-4-chlorobenzenesulfonamide

Procedure

The commercially available p-chlorophenylsulfonyl isocyanate (15.0 g, 58.6 mmol) is added dropwise to t-butanol (90 ml) and the mixture is allowed to stir at room temperature for 60 hours. The solvent is evaporated and the white solid is recrystallized from hexane and ethylacetate to obtain N-t-butoxycarbonyl-p-chlorophenylsulfonamide, m.p. 98°-99° C.

Workup

  1. customThe solvent is evaporated
  2. customthe white solid is recrystallized from hexane and ethylacetate

Sources & evidence

ORD record
ord-c6fefe3fbe4c4b8ba246ce545c3a9649
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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