Methanol → N-tert-butyl-3-chloropropane-1-sulfonamide

HRID 1363017Notes

Reaction equation

HRID 1363017 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].[C:9]([NH2:13])([CH3:12])([CH3:11])[CH3:10].CO>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 6385Tert-ButylamineHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 11701296N-tert-butyl-3-chloropropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloropropanesulfonyl chloride (commercially available, for example, from Aldrich) (1 g, 6 mmol) in DCM (10 ml) in an ice-water bath was added t-butylamine (commercially available, for example, from Aldrich) (1.3 ml, 12 mmol). The solution was allowed to warm to ambient temperature and stirred for 3 h. The reaction mixture was applied to a SCX-2 cartridge (50 g) (preconditioned with methanol) and the cartridge eluted with methanol (2 column volumes). The methanol fraction was concentrated in vacuo to give the title compound as a white waxy solid (1.17 g, 97%). LCMS RT=2.61 min, ES+ve m/z 214 (M+H)+.

Workup

  1. washthe cartridge eluted with methanol (2 column volumes)
  2. concentrationThe methanol fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-74c325f8ed044609bb46e04c0ccfd551
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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