p-Anisoyl chloride → 3-(4-Methoxybenzoyl)-4-oxothiazolidine

Reaction equation

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

Participants

Procedure

A solution of 4-methoxybenzoyl chloride (20.7 g) in tetrahydrofuran (50 ml) was added dropwise to a mixture of 4-oxo-thiazolidine (12.5 g) and triethylamine (16.9 ml) in tetrahydrofuran (200 ml) at -5° C. with stirring. The mixture was stirred at that temperature for 3 hours and at room temperature for 4 hours, and allowed to stand overnight. After the solvent was evaporated in vacuo, the residue was mixed with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and then with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(4-methoxybenzoyl)-4-oxothiazolidine (18.1 g) as slightly brown prisms.