1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-4-oxothiazolidine

Participants

Reaction Steps

A solution of 4-oxothiazolidine (3.00 g) in tetrahydrofuran (40 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (1.28 g) in tetrahydrofuran (30 ml) at room temperature with stirring. 3-Bromo-1-chloropropane (3.15 ml) was added dropwise to the mixture under refluxing and the mixture was allowed to reflux for 9 hours. After the resultant precipitate was removed by filtration, the filtrate was evaporated in vacuo. The residue was chromatographed on basic alumina by eluting with ethyl acetate and then with a 10:1 mixture of toluene and ethyl acetate to give 3-(3-chloropropyl)-4-oxothiazolidine (2.60 g) as colorless oil.

Provenance & Evidence