• Title of article

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

  • Author/Authors

    Eckhardt, Tamira Institut für Pharmazie, Germany , Goddard, Richard Max-Planck-Institut für Kohlenforschung, Germany , Rudolph, Ines Institut für Pharmazie, Germany , Richter, Adrian Institut für Pharmazie, Germany , Lehmann, Christoph Institut für Pharmazie, Germany , Imming, Peter Institut für Pharmazie, Germany , Seidel, Rüdiger W. Institut für Pharmazie, Germany

  • Pages
    10
  • From page
    1
  • To page
    10
  • 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.
  • Keywords
    benzo­thia­zinones , nitro­benzamides , anti-tuberculosis drugs , reaction mechanism , crystal structure
  • Journal title
    Acta Crystallographica Section E: Crystallographic Communications
  • Serial Year
    2020
  • Record number

    2622919