(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(4-methylanilino)-3-(methylsulfanyl)acrylonitrile

Abstract

The title compound, C17H14Cl2N2O2S2, and the 3-methoxy­anilino analogue reported in the preceding paper have been used as starting materials to develop benzothia­zine derivatives with anti­malarial activity. The mol­ecule displays an E (trans) configuration about the central double bond. Due to conjugation in the C=C—C N group, the putative single bond shows a significant shortening [1.418 (3) Å]. The mol­ecule has a six-membered ring involving an intra­molecular N—H⋯O(sulfon­yl) bond, which is an example of resonance-assisted hydrogen bonding. In the crystal structure, bonds of the C—H⋯O(sulfon­yl) and C—H⋯N(cyano) types form double layers of mol­ecules parallel to (01). Within these layers there are π–π inter­actions between benzene rings of pairs of centrosymmetrically related mol­ecules, with distances of 3.7969 (12) Å between centroids. C—H⋯π interactions are also present.

(2E)-2-(2,4-Dichlorophenylsulfonyl)-3-(3-methoxyanilino)-3-(methylsulfanyl)acrylonitrile

“…For related literature, see: Allen (2002); Allen et al (1987); Barazarte et al (2008); Capparelli et al (2008); Charris et al (2005Charris et al ( , 2007; Gilli et al (1989); Kennard et al (2003); Krivokolysko et al (2002); Song et al (2005); Tominaga et al (1989Tominaga et al ( , 2002.…”

“…The exploration of simple molecules with different functionalities for the synthesis of heterocycles is a worthwhile contribution to the chemistry of these compounds. The title compound (I), the 4′′-methyl analogue (II) [see next paper: Capparelli et al, 2008)], and similar derivatives, have been used as effective synthons in the syntheses of some 1Hpyrrole-2,5-diones (Tominaga et al, 2002), pyrimidine derivatives (Tominaga et al, 1989) and 4H-1,4-benzothiazine-1,1dioxides (Charris et al, 2005). We used (I) and (II) as starting materials to develop benzothiazine derivatives with antimalarial activity (Charris et al, 2007;Barazarte et al, 2008).…”