Dimethylformamide → alpha-(p-Tolylthio)(m-benzoylphenyl)acetonitrile

HRID 1759424Notes

Reaction equation

HRID 1759424 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.C[O-].[Na+].CN(C=O)C.C1(C)C=CC(S(O[CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=[O:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:31]=2)[C:28]#[N:29])(=O)=O)=CC=1>CO.O>[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([S:7][CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36](=[O:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:31]=2)[C:28]#[N:29])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 10942334Sodium MethoxideHCID 12945137O-(p-toluenesulfonyl)-m-benzoylmandelonitrile

Product 1

HCID 12945140alpha-(p-Tolylthio)(m-benzoylphenyl)acetonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-15 °C

Procedure

p-Toluenethiol (372 mg) was dissolved in 2 ml of anhydrous methanol, and 1.20 ml of a 2.5 M methanol solution of sodium methoxide was added at room temperature in an atmosphere or argon. The mixture was cooled to -15° C., and stirred. Then, 4 ml of an anhhdrous DMF solution containing 1.170 g of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile was added over 10 minutes. With continued stirring, the mixture was gradually warmed, and in 30 minutes, the temperature rose to 0° C. At this time, 30 ml of water was added to the reaction mixture, and the mixture was extracted with 20 ml of methylene chloride three times. The extract was washed with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene) to afford 837 mg (yield 82%) of alpha-(p-tolylthio)(m-benzoylphenyl)acetonitrile as colorless crystals.

Workup

  1. additionwas added over 10 minutes
  2. stirringWith continued stirring
  3. temperaturethe mixture was gradually warmed
  4. customrose to 0° C
  5. extractionthe mixture was extracted with 20 ml of methylene chloride three times
  6. washThe extract was washed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel; benzene)

Sources & evidence

ORD record
ord-e8271fd0a8914c6fb81039765394a001
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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