Water → HCID 14892625, compound

HRID 614253Notes

Reaction equation

HRID 614253 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.C(N(CC)CC)C.P(Cl)(Cl)([Cl:23])=O.O>C(Cl)Cl>[CH3:1][S:2][C:4]([S:12][CH3:13])=[C:5]([Cl:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 53914774HCID 53914774, compound

Product 1

HCID 14892625HCID 14892625, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

1-Methylsulfinyl-1-methylthio-2-phenylethylene (1.154 g) was dissolved in 15 ml of methylene chloride, and 1 ml of triethylamine was added. Under cooling at -15° C., 0.55 ml of phosphorus oxychloride was added. The mixture was stirred at -15° C. for 1 hour and then at room temperature for 2 hours. Water (30 ml) was added, and the reaction mixture was extracted three times with 30 ml of methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a Florisil column using hexane/benzene as an eluant to afford 1.180 g of 1,1-bis(methylthio)-2-chloro-2-phenylethylene in a yield of 94%.

Workup

  1. waitat room temperature for 2 hours
  2. extractionthe reaction mixture was extracted three times with 30 ml of methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a Florisil column

Sources & evidence

ORD record
ord-98114c1658854475883afca3e2d1a1b4
Source dataset
uspto-grants-1979_03
Patent number
US04144248

Reaction notes

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