Imidazole → HCID 14349376, compound

Participants

Reaction Steps

Thionyl chloride (17.8 g, 0.15 mole) was added dropwise over 30 minutes to 1H-imidazole (41.1 g, 0.60 mole) in dried methylene chloride (200 ml) with stirring and ice-cooling. After stirring for additional 30 minutes, 2-hydroxy-5-fluoroacetophenone (15.4 g, 0.10 mole) in dried methylene chloride (50 ml) was added dropwise over 30 minutes. After stirring for 1 hour, methylene chloride (200 ml), water (400 ml) and an aqueous saturated solution of sodium bicarbonate (200 ml) were added to the reaction mixture and the mixture was stirred for 5 minutes. Then, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from ethyl acetate to obtain the title compound (3.71 g, 18.2%), m.p. 164°-166° C.

Provenance & Evidence