Dichloromethane → HCID 13228938, compound

Participants

Reaction Steps

4-Chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (15 g) was added to 270 ml of a dichloromethane solution containing 16.2 g of aluminum chloride and 10 g of 1,3-ethanedithiol and the mixture was stirred at room temperature, whereupon the starting material dissolved once and then a precipitate separated out. The mixture was allowed to stand at room temperature for 6 hours. The supernatant was then discarded, and 50 ml of acetone and 20 ml of water were added to the precipitate. To the resulting solution was added 20 ml of lN-hydrochloric acid to give a precipitate, which was dissolved in 150 ml of 75% ethanol. The solution was passed through a column of 50 ml of Amberlite IRC-50 (trademark) (H-form) and the column was washed with 75% ethanol. The effluent and washings were combined and diluted with water to the ethanol concentration of 50%. The above procedure gave 12 g of 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless scales, m.p. 190°-192 ° C. (decompn.).

Provenance & Evidence