Methyl iodide → HCID 12945142, compound

HRID 1759429Notes

Reaction equation

HRID 1759429 reaction equation
[C:1]1([CH3:24])[CH:6]=[CH:5][C:4]([S:7][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[O:18])=[CH:13][CH:12]=2)[C:9]#[N:10])=[CH:3][CH:2]=1.[CH3:25][O-].[Na+].CI.[Cl-].[NH4+]>CO>[C:1]1([CH3:24])[CH:2]=[CH:3][C:4]([S:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)=[O:18])=[CH:13][CH:12]=2)([CH3:25])[C:9]#[N:10])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 12945141HCID 12945141, compound

Product 1

HCID 12945142HCID 12945142, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Anhydrous methanol (3 ml) was added to 351 mg of alpha-(p-tolylthio)[p-(2-thienylcabonyl)phenyl]acetonitrile, and the mixture was stirred in an argon atmosphere under ice cooling. Then, 0.45 ml of a 2.5 M methanol solution of sodium methoxide was added, and 0.10 ml of methyl iodide was added dropwise. The temperature was brought to room temperature and the mixture was stirred for 15 minutes. An aqueous solution of ammonium chloride (0.2 g/30 ml) was added, 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; methylene chloride) to afford 314 mg (yield 86%) of alpha-(p-tolylthio)-alpha-[p-(2-thienylcabonyl)phenyl]-propionitrile as colorless crystals.

Workup

  1. customwas brought to room temperature
  2. stirringthe mixture was stirred for 15 minutes
  3. extractionthe mixture was extracted with 20 ml of methylene chloride three times
  4. washThe extract was washed with 20 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationand concentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel; methylene chloride)

Sources & evidence

ORD record
ord-ded3c3db7f004e92822af439b47811f3
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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