Carbon Dioxide → HCID 12898771, compound

HRID 1414016Notes

Reaction equation

HRID 1414016 reaction equation
[SH2:1].[Br-].[Cl:3][C:4]1[CH:20]=[CH:19][C:7]([C:8](=[N+]2CCCCC2)[S:9][CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.C(=O)=O>C(O)C>[C:11]([CH2:10][S:9][C:8](=[S:1])[C:7]1[CH:19]=[CH:20][C:4]([Cl:3])=[CH:5][CH:6]=1)#[N:12]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 402Hydrogen Sulfide3×HCID 12898753HCID 12898753, compound

Product 1

HCID 12898771HCID 12898771, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-20 °C

Procedure

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.

Workup

  1. customrises to 25° C
  2. temperaturechilled condenser
  3. temperatureto warm up to room temperature
  4. customto evaporate overnight
  5. concentrationThe reaction mixture is then concentrated in vacuo

Sources & evidence

ORD record
ord-3951b62943db47bd9bc8be442057dc39
Source dataset
uspto-grants-1981_02
Patent number
US04252814

Reaction notes

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