Acetic Acid → Dibenzothiazepinone

Participants

Reaction Steps

2-(2-Aminophenylthio)benzonitrile (3.72 g, 16 mmol) was dissolved in water (35 ml), acetic acid (35 ml) and concentrated sulphuric acid (35 ml) and stirred and heated under reflux for 3 hr. The mixture was allowed to cool and poured onto crushed ice (600 ml) and adjusted to pH 6 with sodium hydroxide solution (10N). The product was extracted into dichloromethane (700 ml), dried (MgSO4) and evaporated in vacuo. The residue was dissolved in xylene (250 ml) and refluxed in a Dean-Stark apparatus for 72 hr. Filtration of the cold reaction mixture and recrystallisation from ethanol gave the title compound as a white crystals (2.99 g, m.p. 255°-256° C., Rf 0.68, CH2Cl2 /MeOH 19:1).

Provenance & Evidence