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  [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis

Eckhardt, T., Goddard, R., Rudolph, I., Richter, A., Lehmann, C., Imming, P., et al. (2020). [2-Chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone: structural characterization of a side product in benzothiazinone synthesis. Acta Crystallographica Section E: Structure Reports Online, 76(9), 1442-1446. doi:10.1107/S2056989020010658.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-EB75-E Version Permalink: http://hdl.handle.net/21.11116/0000-0006-EB76-D
Genre: Journal Article

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 Creators:
Eckhardt, Tamira1, Author
Goddard, Richard2, Author              
Rudolph, Ines1, Author
Richter, Adrian1, Author
Lehmann, Christoph1, Author
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: benzothiazinones; nitrobenzamides; anti-tuberculosis drugs; reaction mechanism; crystal structure
 Abstract: 1,3-Benzothiazin-4-ones (BTZs) are a promising new class of anti-tuberculosis drug candidates, some of which have reached clinical trials. The title compound, the benzamide derivative [2-chloro-3-nitro-5-(trifluoromethyl)phenyl](piperidin-1-yl)methanone, C13H12ClF3N2O3, occurs as a side product as a result of competitive reaction pathways in the nucleophilic attack during the synthesis of the BTZ 8-nitro-2-(piperidin-1-yl)-6-(trifluoromethyl)-1,3-benzothiazin-4-one, following the original synthetic route, whereby the corresponding benzoyl isothiocyanate is reacted with piperidine as secondary amine. In the title compound, the nitro group and the nearly planar amide group are significantly twisted out of the plane of the benzene ring. The piperidine ring adopts a chair conformation. The trifluoromethyl group exhibits slight rotational disorder with a refined ratio of occupancies of 0.972 (2):0.028 (2). There is structural evidence for intermolecular weak C—H...O hydrogen bonds.

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Language(s): eng - English
 Dates: 2020-07-142020-08-032020-09-01
 Publication Status: Published online
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1107/S2056989020010658
 Degree: -

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Title: Acta Crystallographica Section E: Structure Reports Online
  Abbreviation : Acta Crystallogr., Sect. E: Struct. Rep. Online
Source Genre: Journal
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Publ. Info: Chester, UK : International Union of Crystallography
Pages: - Volume / Issue: 76 (9) Sequence Number: - Start / End Page: 1442 - 1446 Identifier: ISSN: 1600-5368
CoNE: https://pure.mpg.de/cone/journals/resource/954925468297