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5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1)
In the reaction of 7-chloro-1,5-benzodiazepine-2,4-dione with N,N-dimethylformamide/dimethylacetal, the diazepine seven-membered ring undergoes a contraction to form the five-membered ring. The reaction yields two isomers the title compound, C(13)H(14)ClN(3)O(2); the major component has the chlori...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151851/ https://www.ncbi.nlm.nih.gov/pubmed/21837218 http://dx.doi.org/10.1107/S1600536811024706 |
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author | Dardouri, Rachida Rodi, Yousef Kandri Saffon, Natalie Essassi, El Mokhtar Ng, Seik Weng |
author_facet | Dardouri, Rachida Rodi, Yousef Kandri Saffon, Natalie Essassi, El Mokhtar Ng, Seik Weng |
author_sort | Dardouri, Rachida |
collection | PubMed |
description | In the reaction of 7-chloro-1,5-benzodiazepine-2,4-dione with N,N-dimethylformamide/dimethylacetal, the diazepine seven-membered ring undergoes a contraction to form the five-membered ring. The reaction yields two isomers the title compound, C(13)H(14)ClN(3)O(2); the major component has the chlorine-atom substituent in the 5-position of the benzimidazolone ring and the minor component has the chlorine atom in the 6-position. The two isomers form a disordered co-crystal, the chloromethylbenzimidazolone portion of both components are disordered with respect to each other in a 4:1 ratio [the refined ratio is 0.816 (5):0.184 (5)]; the dimethylaminocryloyl substitutent is ordered. The double bond of the dimethylaminoacryloyl substituent has an E configuration. |
format | Online Article Text |
id | pubmed-3151851 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-31518512011-08-11 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) Dardouri, Rachida Rodi, Yousef Kandri Saffon, Natalie Essassi, El Mokhtar Ng, Seik Weng Acta Crystallogr Sect E Struct Rep Online Organic Papers In the reaction of 7-chloro-1,5-benzodiazepine-2,4-dione with N,N-dimethylformamide/dimethylacetal, the diazepine seven-membered ring undergoes a contraction to form the five-membered ring. The reaction yields two isomers the title compound, C(13)H(14)ClN(3)O(2); the major component has the chlorine-atom substituent in the 5-position of the benzimidazolone ring and the minor component has the chlorine atom in the 6-position. The two isomers form a disordered co-crystal, the chloromethylbenzimidazolone portion of both components are disordered with respect to each other in a 4:1 ratio [the refined ratio is 0.816 (5):0.184 (5)]; the dimethylaminocryloyl substitutent is ordered. The double bond of the dimethylaminoacryloyl substituent has an E configuration. International Union of Crystallography 2011-06-30 /pmc/articles/PMC3151851/ /pubmed/21837218 http://dx.doi.org/10.1107/S1600536811024706 Text en © Dardouri et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Dardouri, Rachida Rodi, Yousef Kandri Saffon, Natalie Essassi, El Mokhtar Ng, Seik Weng 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title | 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title_full | 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title_fullStr | 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title_full_unstemmed | 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title_short | 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) |
title_sort | 5-chloro-1-[(e)-3-(dimethylamino)acryloyl]-3-methyl-1h-benzimidazol-2(3h)-one–6-chloro-1-[(e)-3-(dimethylamino)acryloyl]-3-methyl-1h-benzimidazol-2(3h)-one (4/1) |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151851/ https://www.ncbi.nlm.nih.gov/pubmed/21837218 http://dx.doi.org/10.1107/S1600536811024706 |
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