Uses
2,4-Diethyl-9H-thioxanthen-9-one is an important organic intermediate to synthetize substituted thioxanthen products.
Chemical Properties
Yellow to yellow-green solid
Flammability and Explosibility
Not classified
Synthesis
Under nitrogen protection, 300 mL of anhydrous toluene, 28.6 g of trichloromethylbenzene, 86 mg of anhydrous ferric chloride and 20.4 g of dithiosalicylic acid were added to the reaction flask. The reaction system was heated to 100 °C and stirred continuously until thin-layer chromatography (TLC) detection showed that the raw materials had largely disappeared. Subsequently, residual chlorine or hydrogen chloride gas was removed from the system by nitrogen bubbling. The solvent was recovered by distillation under reduced pressure and the residue was distilled under reduced pressure to give 17.6 g of benzoyl chloride. The remaining o-chlorothiobenzoyl chloride intermediate in the flask was mixed with 20.3 g of diethylbenzene and 200 mL of dichloroethane and added slowly and dropwise to a 150 mL solution of dichloroethane containing 23.3 g of anhydrous aluminum trichloride powder. The reaction temperature was maintained at 20°C and the reaction was carried out under effective stirring for half an hour. Subsequently, the reaction mixture was slowly poured into an equal volume of ice-water mixture under rapid mechanical stirring. The organic phase was washed sequentially with water and dilute sodium hydroxide solution and the solvent was evaporated to dryness to give an oily substance. The oil was recrystallized from hot methanol to give 28.6 g of 2,4-diethylthiazolone (DETX).
References
[1] Patent: CN107540580, 2018, A. Location in patent: Paragraph 0018
