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Keywords = unsymmetrical N,N′-diaryl urea

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9 pages, 838 KB  
Short Note
1-[2-(1H-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea
by Antonia G. Sarantou and George Varvounis
Molbank 2023, 2023(1), M1531; https://doi.org/10.3390/M1531 - 22 Dec 2022
Cited by 1 | Viewed by 4513
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 [...] Read more.
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. Full article
(This article belongs to the Collection Heterocycle Reactions)
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