Thionyl Chloride → HCID 13590116, compound

Participants

Reaction Steps

The requisite 1-chloro-7-methoxy-4-nitrothioxanthone was prepared as follows: A mixture of 118.5 g (0.35 mole) of 2-(5-chloro-2-nitrophenylthio)-5-methoxybenzoic acid and 131 ml of thionyl chloride in 600 ml of toluene was heated under reflux for 1.5 hours. The mixture was concentrated in vacuo, and the resulting solid was dissolved in 950 ml of nitrobenzene with heating and then cooled to 0° in an ice bath. Aluminum chloride (44.2 g) was added in portions over 0.5 hour with cooling, and the mixture was then allowed to come to room temperature and stirred overnight. The mixture was poured into 5 l of cold water. As much of the water layer as possible was decanted. The residue was triturated twice with 1 l portions of methanol and then twice with 2 l portions of methanol. The oil was triturated with 4 l of methanol and a solid resulted. This was washed with methanol and dried in vacuo at 75° to give 72.7 g of the product as a brownish-yellow solid, mp 235°-240°.

Provenance & Evidence