4-Methoxybenzenesulfonyl chloride → 3-(4-Methoxybenzenesulfonyl)-4-oxothiazolidine

Reaction equation

[H-].[Na+].[O:3]=[C:4]1[CH2:8][S:7][CH2:6][NH:5]1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>O1CCCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([N:5]2[C:4](=[O:3])[CH2:8][S:7][CH2:6]2)(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

Procedure

Sodium hydride (60% dispersion in mineral oil) (0.58 g) was added portionwise to a solution of 4-oxothiazolidine (1.50 g) and 4-methoxybenzenesulfonyl chloride (3.01 g) in tetrahydrofuran (30 ml) at 0° C. with stirring and the mixture was stirred for 1 hour at the same temperature. After the solvent was evaporated in vacuo, the residue was mixed with ethyl acetate (10 ml) and water (50 ml) and the resultant precipitate was collected by filtration. The cake was washed with water and diisopropyl ether and recrystallized from a mixture of ethanol and ethyl acetate to give 3-(4-methoxybenzenesulfonyl)-4-oxothiazolidine (1.65 g) as slightly brown prisms.