Tetrahydrofuran → HCID 15136147, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.24 ml of trichloromethyl chloroformate (TCF) and 15 ml of tetrahydrofuran is stirred at 60° C. for 2 hours, cooled with ice, mixed with 412 mg of thiomorpholine, and the mixture is stirred for 1 hour at room temperature. The reaction mixture is cooled with ice again and mixed with 1.212 g of triethylamine. The mixture is stirred at room temperature for 1 hour, mixed with 500 mg of 3-ethoxycarbonyl-9-mercapto-4H-quinolizin-4-one (II-3), and the mixture is stirred at room temperature for 17 hours. The reaction mixture is filtered, and the filtrate is concentrated. The residue is chromatographed on a column of 10 g of silica gel, eluting with methylene chloride-methanol (19:1 v/v). The resultant crystals are recrystallized from ethyl acetate to give 321 mg (Yield: 42.3%) of 3-ethoxycarbonyl-9-(thiomorpholinocarbonylthio)-4H-quinolizin-4-one (I a-6).

Provenance & Evidence