Potassium Carbonate → N-benzyloxy-3-chloropropylsulfonamide

HRID 1060834Notes

Reaction equation

HRID 1060834 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].Cl.[CH2:10]([O:17][NH2:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.O.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:10]([O:17][NH:18][S:5]([CH2:4][CH2:3][CH2:2][Cl:1])(=[O:7])=[O:6])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 154103-Chloropropanesulphonyl chlorideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 10539517N-benzyloxy-3-chloropropylsulfonamideYield 41%

Reagents, catalysts & solvents 3

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Chloropropylsulfonyl chloride 1 (30.28 g, 0.17 mol), O-benzylhydroxylamine hydrochloride (27.3 g, 0.17 mol), potassium carbonate (50 g, 0.36 mol) and tetrabutylammonium sulfate (about 500 mg) are reacted in a mixture of ether (1L) and water (100 ml) for 24 hours at room temperature and the reaction mixture was extracted with ethyl acetate. The extract was subjected to column chromatography on silica gel. From the fraction eluted with a mixture of ethyl acetate/n-hexane (1:4), 18.4 g (41%) of crude N-benzyloxy-3-chloropropylsulfonamide (intermediate 3g) was obtained as a pale yellow oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washFrom the fraction eluted with a mixture of ethyl acetate/n-hexane (1:4)

Sources & evidence

ORD record
ord-64462de2831b40ebaa23203828295d4c
Source dataset
uspto-grants-2003_02
Patent number
US06525081B1

Reaction notes

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