Reaction #63187

Reaction equation

4-methoxybenzoyl chloride

4-oxo-thiazolidine

triethylamine

→

3-(4-methoxybenzoyl)-4-oxothiazolidine

Yield 62.9%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGThe mixture was stirred at that temperature for 3 hours and at room temperature for 4 hours
2. 2
   OtherAfter the solvent was evaporated in vacuo
3. 3
   workup.ADDITIONthe residue was mixed with water
4. 4
   Extractionextracted with ethyl acetate
5. 5
   WashThe extract was washed with saturated aqueous sodium hydrogen carbonate
6. 6
   Dryingwith water, dried over magnesium sulfate
7. 7
   Otherevaporated in vacuo
8. 8
   OtherThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

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.

Source