Phenyl isocyanate → HCID 13588450, compound

Participants

Reaction Steps

Under a nitrogen atmosphere a stirred solution of 4-amino-1H-imidazole-5-carbonitrile (1.1 g, 0.01 mole) and phenyl isocyanate (1.3 g, 0.011 mole) in 30 ml of dry methyl ethyl ketone was heated under reflux for 10 hours. The solvent was removed, and the residue was stirred with 50 ml of boiling tetrahydrofuran. The mixture was filtered hot, and the filtrate was concentrated under reduced pressure. The residual solid was slurried in 50 ml of diethyl ether and the solid was collected by filtration, washed three times with diethyl ether, and dried to give a solid (1.2 g; mp, 165° d). The solid was dissolved in hot ethanol/toluene and an insoluble material removed by filtration. The filtrate was concentrated under reduced pressure to give N-phenyl-N'-(5-cyano-1H-imidazol-4-yl)urea (0.93 g; mp, >300°).

Provenance & Evidence