Trichloroacetyl isocyanate → HCID 57545312, compound

Participants

Reaction Steps

A modification of the general method described in Part C of Example 3 was followed using 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline (2.6 g, 6.4 mmol) as the starting material and chloroform as the solvent. The reaction with trichloroacetyl isocyanate was not complete after one hour as evidenced by a TLC analysis. Additional trichloroacetyl isocyanate was added, and the reaction was stirred overnight. Following the reaction with sodium methoxide, the solid product was isolated by filtration and washed with methanol and a mixture of dichloromethane and water. The solid was isolated by filtration and recrystallized from 2-methoxyethyl ether. The crystals were dried under high vacuum to provide 8-benzyloxy-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 183-184° C.

Provenance & Evidence