Butanethiol → alpha-(Butylthio)(m-benzoylphenyl)-acetonitrile

HRID 1759432Notes

Reaction equation

HRID 1759432 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][CH3:4].C[O-].[Na+].COCCOC.C1(C)C=CC(S(O[CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:29]=2)[C:26]#[N:27])(=O)=O)=CC=1>CO.O>[CH2:1]([S:5][CH:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:29]=1)[C:26]#[N:27])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 8012ButanethiolHCID 80711,2-DimethoxyethaneHCID 10942334Sodium MethoxideHCID 12945137O-(p-toluenesulfonyl)-m-benzoylmandelonitrile

Product 1

HCID 20532026alpha-(Butylthio)(m-benzoylphenyl)-acetonitrileYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Butylmercaptan (105 mg) was dissolved in 1 ml of methanol, and 0.4 ml of a 2.7 M methanol solution of sodium methoxide was added at room temperature. The solution was added dropwise to 2 ml of a 1,2-dimethoxyethane solution of 391 mg of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile in an argon atmosphere under ice cooling. The mixture was stirred for 1 hour under ice cooling, and 20 ml of water was added. The mixture was extracted with 20 ml of methylene chloride three times. The extract was washed with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (silica gel; benzene) to afford 95 mg (yield 31%) of alpha-(butylthio)(m-benzoylphenyl)acetonitrile as a colorless oil.

Workup

  1. extractionThe mixture was extracted with 20 ml of methylene chloride three times
  2. washThe extract was washed with 10 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated by column chromatography (silica gel; benzene)

Sources & evidence

ORD record
ord-ce992711740449279ad3ff567bf10400
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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