Reaction #1909811

Reaction equation

thiobenzamide

1,3-dichloroacetone

→

4-chloromethyl-2-phenylthiazole

Yield 57.0%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureunder reflux for 1 hour
2. 2
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure, and ice water
3. 3
   workup.ADDITIONwas added to the remaining product, which
4. 4
   ExtractionThe resulting product was extracted with ethyl acetate
5. 5
   Washwashed with saturated saline
6. 6
   Dryingdried over sodium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   OtherThe residual product was purified through silica gel column chromatography

Procedure

2.33 g of thiobenzamide was dissolved in 20 ml of dry methanol, and 2.16 g of 1,3-dichloroacetone was added thereto at room temperature and then heated under reflux for 1 hour. The solvent was distilled off under reduced pressure, and ice water was added to the remaining product, which was then neutralized with an aqueous solution of sodium hydrogen carbonate. The resulting product was extracted with ethyl acetate, washed with saturated saline, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 2.03 g of 4-chloromethyl-2-phenylthiazole, was obtained from the fraction eluted with chloroform/n-hexane=1/2.

Source