1-Adamantanecarbonyl chloride → 5-Carbamoyl-1H-imidazol-4-yl-1-adamantanecarboxylate

Participants

Reaction Steps

To a solution of 1-adamantanecarbonylchloride (39.73 g) in pyridine (260 ml) was added 4-carbamoylimidazolium-5-olate (12.71 g) and the reaction temperature was maintained at 41°-43° C. for 3.5 hours. Pyridine was removed under reduced pressure. To the residue was added ethylacetate (300 ml) and water (300 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 (25.9 g, β form, m.p. 205°-205.5° C. (dec.)). Recrystallization from dimethylformamide-diethylether gave analytically pure sample (β form m.p. 213.5°-216.5° C. (dec.)).

Provenance & Evidence