Fluorine → HCID 11034512, compound

Participants

Reaction Steps

The synthetic intermediate imine (Z)—N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride (a pale yellow oil) was prepared as described in Huang et al., J. Fluorine Chem., 74:279-282 (1995) and used without distillation. To ethyl isocyanoacetate (0.467 g, 4.13 mmol) in dry THF (50 mL) was added NaH (170 mg, 4.13 mmol, 60% dispersed in oil) at 0° C. and after 5 minutes, (Z)—N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride (1.0 g, 4.13 mmol). The reaction mixture was allowed to warm to room temperature. The mixture was purified using an 80 g SiO2 column and a 10-100% EtOAc/hexanes gradient. Obtained 900 mg (68% yield) of ethyl 1-(4-chlorophenyl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate as a pale yellow solid. This compound matched the 1H NMR found in the J. Fluorine Chem. reference.

Provenance & Evidence