(Ethylsulfonyl)ethene → HCID 53685976, compound

HRID 2058991Notes

Reaction equation

HRID 2058991 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[CH:4][CH:3]=1.[CH:10]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH2:11]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:11]=[CH:10][S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74680(Ethylsulfonyl)etheneHCID 110844654-Chlorobenzenesulfenylchloride

Product 1

HCID 53685976HCID 53685976, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-chlorophenylsulfenyl chloride, 7.5 g was added to 5.0 g of ethyl vinyl sulfone in 20 ml of dichloromethane. There was no exotherm and the system was refluxed for 3 hours. The dichloromethane was removed by stripping and the residue was dissolved in 50 ml of benzene. Triethylamine, 4.2 g, was added dropwise with cooling and after standing for 1 hour, the triethylamine hydrochloride was removed by filtration and the benzene stripped to give a crude product. Purification was carried out by chromatography on a silica gel column. The product, ethyl 2-(4-chlorophenylthio)vinyl sulfone, 4.2 g, was obtained as a clear oil showing one spot by thin-layer chromatography.

Workup

  1. temperaturethe system was refluxed for 3 hours
  2. customThe dichloromethane was removed
  3. dissolutionthe residue was dissolved in 50 ml of benzene
  4. additionTriethylamine, 4.2 g, was added dropwise
  5. temperaturewith cooling
  6. customthe triethylamine hydrochloride was removed by filtration
  7. customto give a crude product
  8. customPurification

Sources & evidence

ORD record
ord-badbcc4d36dc40f097cde0e8181dc286
Source dataset
uspto-grants-1982_03
Patent number
US04321080

Reaction notes

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