Propyl mercaptan → HCID 15136157, compound

Participants

Reaction Steps

To a suspension of 0.395 g of 60% sodium hydride (mineral oil dispersion) in 20 ml of anhydrous tetrahydrofuran is added 0.82 ml of n-propyl mercaptan under ice-cooling. After stirring for 30 minutes, the resultant mixture is mixed with 2.634 g of 3-ethoxycarbonyl-9-dimethylcarbamoylthio-4H-quinolizin-4-one in 40 ml of tetrahydrofuran, and stirred at room temperature for another 15 hours. The reaction mixture is mixed with 8 ml of aqueous sodium hypochlorite and extracted with methylene chloride. The organic layer is washed with water, dried over sodium sulfate and concentrated to give a residue, which is chromatographed on a column of 30 g of silica gel eluting with methylene chloride-methanol (9:1 v/v) to give crude product, which is recrystallized from ethyl acetate to give 1.153 g (Yield: 56.3%) of 3-ethoxycarbonyl-9-mercapto-4H-quinolizin-4-one.

Provenance & Evidence