1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea

Abstract

For the synthesis of 1-(2-(1H-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1H-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction with 1/3 equivalent of triphosgene in the presence of two equivalents of trimethylamine, followed by the addition of 4-methoxyaniline to the in situ generated aryl isocyanate. The two-step synthesis required first the preparation of phenyl(2-(1H-pyrrole-2-carbonyl)phenyl)carbamate and then a substitution reaction by 4-methoxyaniline. The first method produced the final product in 72% yield, which was the best yield. The structure of the final product was confirmed by FTIR, UV-VIS, 1H and 13C NMR spectroscopy and high resolution mass spectrometry.

Keywords

• heterocycle
• unsymmetrical <i>N</i>,<i>N</i>′-diaryl urea
• carbonylation
• triphosgene
• carbamate