Methyl iodide → HCID 54078109, compound

HRID 1759425Notes

Reaction equation

HRID 1759425 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[C:9]#[N:10])=[CH:3][CH:2]=1.[CH3:26][O-].[Na+].CI.[Cl-].[NH4+]>CO>[C:1]1([CH3:25])[CH:2]=[CH:3][C:4]([S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:12]=2)([CH3:26])[C:9]#[N:10])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 12945140alpha-(p-Tolylthio)(m-benzoylphenyl)acetonitrile

Product 1

HCID 54078109HCID 54078109, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Anhydrous methanol (2 ml) was added to 439 mg of alpha-(p-tolylthio)(m-benzoylphenyl)acetonitrile, and the mixture was stirred under ice cooling. Then, 0.55 ml of a 2.5 M methanol solution of sodium methoxide was added, and 0.12 ml of methyl iodide was added dropwise. The mixture was further stirred for 30 minutes at room temperature. An aqueous solution of ammonium chloride (0.5 g/20 ml) was added, and the mixture was extracted with 15 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 to afford an oily residue. The residue was purified by column chromatography (silica gel; benzene) to afford 422 mg (yield 92%) of alpha-(p-tolylthio)-alpha-(m-benzoylphenyl)propionitrile as a colorless oil.

Workup

  1. stirringThe mixture was further stirred for 30 minutes at room temperature
  2. extractionthe mixture was extracted with 15 ml of methylene chloride three times
  3. washThe extract was washed with 10 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford an oily residue
  7. customThe residue was purified by column chromatography (silica gel; benzene)

Sources & evidence

ORD record
ord-d757711c2dd8493a8dd3e9061032164e
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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