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Updated: May 13, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,6-Dichloro-aniline-4-(2,6-dichloro-anilino)-pent-3-en-2-one (1/2)
Gertruida J S Venter1, Gideon Steyl, Andreas Roodt
1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa.
Abstract:
The asymmetric unit of the title compound, C6H5Cl2N·2C11H11Cl2NO, is composed of one mol-ecule of an enamino-ketone [i.e. -(2,6-dichloro-phenyl-amino)-pent-3-en-2-one] and half a mol-ecule of 2,6-dichloro-aniline, the whole mol-ecule of the latter component being generated by twofold rotational symmetry. In this latter mol-ecule, there are two intra-molecular N-H⋯Cl contacts. In the enamino-ketone mol-ecule, there is an N-H⋯O hydrogen bond of moderate strength, and the dihedral angle between the benzene ring and penta-none fragment [C-C(-N)=C-C(=O)-C; planar within 0.005 (1) Å] is 81.85 (7)°. In the crystal, two mol-ecules of the enamino-ketone are bridged by a mol-ecule of 2,6-dichloro-aniline via N-H⋯O hydrogen bonds of moderate strength. There are also π-π inter-actions present, involving the benzene rings of inversion-related enamino-ketone mol-ecules [centroid-centroid distance = 3.724 (4) Å].
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