Formation of N-acyl-N,N′-dicyclohexylureas from DCC and Arenecarboxylic Acids in the Presence of Hydroxybenzotriazole in CH2Cl2 at Room Temperature

Abstract

The syntheses of N-acyl- N,N′-dicyclohexylureas from 1,3-dicyclohexylcarbodiimide and arenecarboxylic acids [ p-XC6H4CO2H (X = H or NO2), 2-, 3- or 4-pyridinecarboxylic acid and pyrazinecarboxylic acid] in the presence of hydroxybenzotriazole in CH2Cl2 at room temperature are reported. The reactions proceed via the intermediacy of O-acyl- N,N′-dicyclohexylurea derivatives which undergo rapid O-acyl to N-acyl rearrangements. No acid anhydrides were detected. Under the same reaction conditions, the O-acyl derivative from the alkanecarboxylic acid, N-(benzyloxycarbonyl)- DL-pipecolic acid does not undergo rearrangement, as shown by the subsequent reaction with MeOH to give methyl N-(benzyloxycarbonyl)- DL-pipecolate. Characterisations were generally achieved by spectroscopic means, and specifically for N-( p-nitrobenzenecarbonyl)- N,N′-dicyclohexylurea by X-ray crystallography.