Reaction #65155

Reaction equation

3-Chloropropylsulfonyl chloride

3-chloropropylsulfonyl chloride

O-benzylhydroxylamine hydrochloride

potassium carbonate

→

N-benzyloxy-3-chloropropylsulfonamide

Yield 41.0%

Solvents

water

ether

Conditions

Workup

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

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 with each other in a mixture of ether and water (1:1) (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.

Source