Divinyl sulfone → 1-Chloro-4-{[2-(ethenesulfonyl)ethenyl]sulfanyl}benzene

HRID 437600Notes

Reaction equation

HRID 437600 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]([CH:15]=[CH2:16])(=[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]([CH:15]=[CH2:16])(=[O:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6496Divinyl sulfoneHCID 110844654-Chlorobenzenesulfenylchloride

Product 1

HCID 537872191-Chloro-4-{[2-(ethenesulfonyl)ethenyl]sulfanyl}benzeneYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fifty grams of 4-chlorophenylsulfenyl chloride was added slowly to 33.0 g of divinyl sulfone in 150 ml of dichloromethane with cooling to remove the heat of reaction. After a few hours of standing at ambient temperature, the solvent was stripped and the crude adduct was dissolved in 200 ml of benzene. Thirty-one g of triethylamine was added slowly with cooling to maintain ambient temperature. After standing for one hour, the triethylamine hydrochloride was removed by filtration. After washing with water and drying over magnesium sulfate, the solvent was stripped to give 64 g of crude product. This was purified by chromatography over silica gel to give 48 g of vinyl 2-(4-chlorophenylthio)vinyl sulfone; calculated for C10HgCl02S2 :S, 24.6; found: S, 24.4.

Workup

  1. temperaturewith cooling
  2. customto remove the
  3. temperatureheat of reaction
  4. waitAfter a few hours of standing at ambient temperature
  5. dissolutionthe crude adduct was dissolved in 200 ml of benzene
  6. additionThirty-one g of triethylamine was added slowly
  7. temperaturewith cooling
  8. customthe triethylamine hydrochloride was removed by filtration
  9. washAfter washing with water
  10. dry with materialdrying over magnesium sulfate
  11. customto give 64 g of crude product
  12. customThis was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-6ec79f5fa6c6410696e1e615f86989e4
Source dataset
uspto-grants-1977_06
Patent number
US04031247

Reaction notes

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