Ethanethiol → HCID 19808776, compound

Participants

Reaction Steps

690 mg of anhydrous aluminum chloride was suspended in 100 ml of methylene chloride. To the suspension was added 1.1 ml of ethanethiol at room temperature, and the mixture was stirred at the same temperature for 30 minutes. Thereto was dropwise added, in 1 minute, a solution of 380 mg of 2-(2-dimethylaminoethyl)-9-methoxy-5-methyl-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione dissolved in 100 ml of methylene chloride. The mixture was stirred at room temperature overnight. The solvent was removed by distillation under reduced pressure. The residue was mixed with 100 ml of ethyl acetate and 50 ml of an aqueous saturated sodium hydrogencarbonate solution. The mixture was stirred for 30 minutes. The resulting insoluble material was removed by filtration. The separated insoluble material was washed with 50 ml of ethyl acetate. The filtrate and the washings were combined. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 340 mg (yield: 93%) of 2-(2-dimethylaminoethyl)-9-hydroxy-5-methyl-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione as yellow crystals.

Provenance & Evidence