Sulfuric Acid → Acemetacin

Participants

Reaction Conditions

Reaction Steps

25 g of indometacin, 10 g of potassium carbonate and 190 ml of acetone are stirred at 56° C. for 30 minutes. The mixture is cooled down to 40° C., 0.5 g of benzyltriethylammonium chloride is added, and 15.6 g of tert.-butyl chloroacetate are added dropwise. After 5 hours at 40° C. the reaction is complete (monitored by thin layer chromatography). The mixture is cooled down to 10° C. and 20 ml of concentrated sulphuric acid are then added dropwise in such a way that the temperature does not exceed 25° C. The mixture is stirred at 20° and 25° C. for 6 hours (monitored by thin layer chromatography), about 500 ml of water are added, and the solids are filtered off with suction, are dried in vacuo and are recrystallized from acetone-water.

Provenance & Evidence