Triethylamine → 1,1-Bis(methylthio)-2-chloro-2-(p-isobutylphenyl) ethylene
Reaction equation
[CH3:1][S:2]([C:4]([S:16][CH3:17])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.S(Cl)([Cl:27])=O>C(Cl)(Cl)Cl>[CH3:1][S:2][C:4]([S:16][CH3:17])=[C:5]([Cl:27])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:8][CH:7]=1Participants
Procedure
1-Methylsulfinyl-1-methylthio-2-(p-isobutylphenyl)ethylene (701 mg) was dissolved in 2 ml of chloroform, and 0.50 ml of triethylamine was added. With stirring under ice cooling, 5 ml of a chloroform solution of 380 mg of thionyl chloride was added over the course of 10 minutes. The mixture was further stirred for 30 minutes under ice cooling, and chloroform was added in an amount sufficient to adjust the total amount of the mixture to 30 ml. The mixture was then washed twice with 10 ml of water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and chromatographed on a Florisil (chromatographic magnesium silicate) column using benzene as an eluent to afford 628 mg of 1,1-bis(methylthio)-2-chloro-2-(p-isobutylphenyl) ethylene as a colorless oil in a yield of 84%.
Workup
- stirringThe mixture was further stirred for 30 minutes under ice cooling
- washThe mixture was then washed twice with 10 ml of water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customchromatographed on a Florisil (chromatographic magnesium silicate) column
Sources & evidence
- ORD record
- ord-a4718ca17c7f428a989cc76f90b9bad9
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04308208
Reaction notes
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