1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea
For the synthesis of 1-(2-(1<i>H</i>-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1<i>H</i>-pyrrol-2-yl)methanone. The one-step synthesis entailed a carbonylation reaction wit...
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MDPI AG
2022-12-01
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| Online Access: | https://www.mdpi.com/1422-8599/2023/1/M1531 |
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| author | Antonia G. Sarantou George Varvounis |
| author_facet | Antonia G. Sarantou George Varvounis |
| author_sort | Antonia G. Sarantou |
| collection | DOAJ |
| description | For the synthesis of 1-(2-(1<i>H</i>-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1<i>H</i>-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-(1<i>H</i>-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, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and high resolution mass spectrometry. |
| first_indexed | 2024-03-11T06:08:28Z |
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| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-11T06:08:28Z |
| publishDate | 2022-12-01 |
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| spelling | doaj.art-92ebe0c57f3e41cd9b04573d0eff15082023-11-17T12:49:01ZengMDPI AGMolbank1422-85992022-12-0120231M153110.3390/M15311-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)ureaAntonia G. Sarantou0George Varvounis1Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 451 10 Ioannina, GreeceSection of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 451 10 Ioannina, GreeceFor the synthesis of 1-(2-(1<i>H</i>-pyrrole-2-carbonyl)phenyl)-3-(4-methoxyphenyl)urea, the final product, two different methods were used, in one or two steps, from (2-aminophenyl)(1<i>H</i>-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-(1<i>H</i>-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, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and high resolution mass spectrometry.https://www.mdpi.com/1422-8599/2023/1/M1531heterocycleunsymmetrical <i>N</i>,<i>N</i>′-diaryl ureacarbonylationtriphosgenecarbamate |
| spellingShingle | Antonia G. Sarantou George Varvounis 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea Molbank heterocycle unsymmetrical <i>N</i>,<i>N</i>′-diaryl urea carbonylation triphosgene carbamate |
| title | 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea |
| title_full | 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea |
| title_fullStr | 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea |
| title_full_unstemmed | 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea |
| title_short | 1-[2-(1<em>H</em>-Pyrrole-2-carbonyl)phenyl]-3-(4-methoxyphenyl)urea |
| title_sort | 1 2 1 em h em pyrrole 2 carbonyl phenyl 3 4 methoxyphenyl urea |
| topic | heterocycle unsymmetrical <i>N</i>,<i>N</i>′-diaryl urea carbonylation triphosgene carbamate |
| url | https://www.mdpi.com/1422-8599/2023/1/M1531 |
| work_keys_str_mv | AT antoniagsarantou 121emhempyrrole2carbonylphenyl34methoxyphenylurea AT georgevarvounis 121emhempyrrole2carbonylphenyl34methoxyphenylurea |