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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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 Urheber:
Eckhardt, Tamira1, Autor
Goddard, Richard2, Autor           
Rudolph, Ines1, Autor
Richter, Adrian1, Autor
Lehmann, Christoph1, Autor
Imming, Peter1, Autor
Seidel, Rüdiger W.1, Autor
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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Schlagwörter: benzothiazinones; nitrobenzamides; anti-tuberculosis drugs; reaction mechanism; crystal structure
 Zusammenfassung: 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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Sprache(n): eng - English
 Datum: 2020-07-142020-08-032020-09-01
 Publikationsstatus: Online veröffentlicht
 Seiten: 5
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.1107/S2056989020010658
 Art des Abschluß: -

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Titel: Acta Crystallographica Section E: Structure Reports Online
  Kurztitel : Acta Crystallogr., Sect. E: Struct. Rep. Online
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Chester, UK : International Union of Crystallography
Seiten: - Band / Heft: 76 (9) Artikelnummer: - Start- / Endseite: 1442 - 1446 Identifikator: ISSN: 1600-5368
CoNE: https://pure.mpg.de/cone/journals/resource/954925468297