Thionyl Chloride → HCID 14892625, compound

HRID 614252Notes

Reaction equation

HRID 614252 reaction equation
[CH3:1][S:2]([C:4]([S:12][CH3:13])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.S(Cl)([Cl:16])=O>C(Cl)Cl>[CH3:1][S:2][C:4]([S:12][CH3:13])=[C:5]([Cl:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53914774HCID 53914774, compound

Product 1

HCID 14892625HCID 14892625, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Methylsulfinyl-1-methylthio-2-phenylethylene (1.868 g) was dissolved in 10 ml of methylene chloride, and with stirring under ice cooling, a solution consisting of 0.71 ml of thionyl chloride and 6 ml of methylene chloride was added dropwise over the course of 30 minutes. Under ice cooling, the mixture was stirred for 1.5 hours, and concentrated under reduced pressure. The residue was chromatographed on a Florisil column using benzene/hexane as an eluant to afford 1.494 g of 1,1-bis(methylthio)-2-chloro-2-phenylethylene as a colorless oil.

Workup

  1. additionwas added dropwise over the course of 30 minutes
  2. stirringUnder ice cooling, the mixture was stirred for 1.5 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on a Florisil column

Sources & evidence

ORD record
ord-3a7d81015cbe40d79d8d4d25cdcd5340
Source dataset
uspto-grants-1979_03
Patent number
US04144248

Reaction notes

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