Triethylamine → 5-carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate

Participants

Reaction Steps

To a suspension of 4-carbamoylimidazolium-5-olate (1.016 g) in dimethylformamide (20 ml) was added triethylamine (1.942 g) at 0°-5° C. and then 1-adamantanecarbonylchloride (3.50 g) in dimethylformamide (20 ml) dropwisely over 24 minutes. The reaction mixture was stirred at 0°-5° C. for 23 hours. The solvent was removed under reduced pressure. To the residue was added ethyl acetate (20 ml) and water (20 ml), and stirred at room temperature for 1 hour. The insoluble solid was filtered and washed with ethyl acetate to give almost pure 5-carbamoyl-1H-imidazol-4-yl 1-adamantanecarboxylate (1.5 g, α form, m.p. 206.5°-207.5° C. (dec.)), which was washed thoroughly with ethyl acetate to give pure product, α form, m.p. 211° C. (dec.).

Provenance & Evidence