Cyclohexyl isocyanate → HCID 9847217, compound

Participants

Reaction Steps

A solution of 5.5 g (16.2 mmol) of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-1-methyl-imidazole in 70 mL of THF was cooled in a −78° C. bath and 15 mL of 1.6 M n-BuLi was slowly added. After stirring for 1 h, 5.2 mL (40.7 mmol) of cyclohexylisocyanate was added. The cooling bath was removed and the solution was stirred for 3 h. The reaction mixture was poured into a mixture of water/EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 2-10% EtOAc-hexane. The isolated product was crystallized from EtOAc-hexane (˜1:10) to obtain the title compound as a white solid with a melting point of 165° C.

Provenance & Evidence