Chloride → 2-Ethylisothiazolidine 1,1-dioxide

Participants

Reaction Steps

To a solution of 24 g of chloride of 3-chloropropanesulfonic acid in 150 ml ethyl ether is added drop-by-drop a solution of 12 g ethylamine and 10 ml ethyl ether. The addition of the ethylamine solution is carried out under stirring and with cooling with the aid of an ice bath. After addition of the solution, the stirring is continued for 1 hour. A white precipitate of ethylamine chlorhydrate forms, which is removed by filtration upon fritted glass. Ethyl ether is removed by evaporation under reduced pressure and, to the residue obtained, is added a mixture of 4.8 g soda pellets, 400 ml ethanol and 12.5 g triethylamine. The mixture is subjected to reflux for 2 hours. After cooling, the solvent is evaporated and the residue is distilled under vacuum. There is obtained 14.2 g (yield: 70%) of N-ethylpropanesultam (boiling point under 0.1 torr: 88° C.).

Provenance & Evidence