Carbon Dioxide → HCID 12898771, compound

Participants

Reaction Conditions

Reaction Steps

Hydrogen sulfide gas is added to a stirred suspension of 1-[p-chloro-α-(cyanomethylthio)benzylidene]piperidinium bromide (13.7 g; 0.037 mol) in ethanol (50 ml), using a dry ice condenser to contain the gas. The reaction mixture slowly becomes a clear, red solution and the temperature rises to 25° C. The reaction mixture is chilled to -20° C., and an excess of hydrogen sulfide is maintained in the reaction mixture for 3 hours, as evidenced by the condensation of same throughout this period in the dry ice, chilled condenser. The reaction mixture is then allowed to warm up to room temperature, and the excess hydrogen sulfide allowed to evaporate overnight. The reaction mixture is then concentrated in vacuo to yield 8.9 g of a red oil. The red oil is chromatographed on silica gel (300 g) and eluted with a 1:1 mixture of methylene chloride:hexane. Collection of the main fraction affords 4.25 g (50%) of title product, a red oil.

Provenance & Evidence