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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...

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Autores principales: Dardouri, Rachida, Rodi, Yousef Kandri, Saffon, Natalie, Essassi, El Mokhtar, Ng, Seik Weng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
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.
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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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