General procedure for the synthesis of 2-(2-chloroethoxy)acetamide from 2-(2-hydroxyethoxy)acetamide:
(b) To a 1 mL chloroform solution containing 535 mg of N-[3-(4-thienyl)]-2-(2-hydroxyethoxy)acetamide, 300 mg of thionyl chloride was slowly added dropwise at 5 °C. The reaction temperature was kept below 10°C and stirred for 1 hour. Subsequently, the reaction mixture was continued to be stirred at room temperature for 1 hour. After completion of the reaction, the mixture was cooled to below 10 °C and weakly acidified with 0.6 g of pyridine. To this solution, 15 mL of chloroform and 15 mL of water were added and the organic layer was separated by stirring. The chloroform layer was washed with water, dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give 0.52 g of brown liquid product in 91% yield.IRν (liquid, cm-1): 3390 (NH), 1675, 1520 (NHCOCH2-).
