Dimethylamine → 5-chloro-N,N-dimethylpentane-1-sulfonamide

A 50% aqueous solution of dimethylamine (5.95 g, 66 mmol) was added dropwise to a solution of diethyl ether (60 ml) and 5-chloropentanesulfonyl chloride (6.15 g, 30 mmol) with stirring under ice-cooling. Thereafter, the mixture was stirred at the same temperature for 20 minutes. The reaction solution was washed twice with water (10 ml) and then with brine (10 ml), and thereafter dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by evaporation in vacuo. The crude product was purified by column chromatography on silica gel with ethyl acetate-n-hexane (1:4), to give N,N-dimethyl-5-chloropentanesulfonamide (6.10 g) as a pale yellow oil.

1. temperaturecooling
2. stirringThereafter, the mixture was stirred at the same temperature for 20 minutes
3. washThe reaction solution was washed twice with water (10 ml)
4. dry with materialwith brine (10 ml), and thereafter dried over anhydrous magnesium sulfate
5. customSubsequently, the solvent was removed by evaporation in vacuo
6. customThe crude product was purified by column chromatography on silica gel with ethyl acetate-n-hexane (1:4)

ORD record

ord-c85b37a9dc244bc096ca2b8a93c0a7eb

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172228B2