Ammonium Chloride → 2-(3-Benzoylphenyl)propanenitrile

HRID 1759435Notes

Reaction equation

HRID 1759435 reaction equation
C1(C)C=CC(S[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)([CH3:11])[C:9]#[N:10])=CC=1.C[S-].[Na+].[Cl-].[NH4+]>CO>[C:18]([C:14]1[CH:13]=[C:12]([CH:8]([CH3:11])[C:9]#[N:10])[CH:17]=[CH:16][CH:15]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 54078109HCID 54078109, compound

Product 1

HCID 393252-(3-Benzoylphenyl)propanenitrileYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

314 mg of alpha-(p-tolylthio)-alpha-(m-benzoylphenyl)propionitrile was dissolved in 1 ml of methanol, and 1.0 ml of a 2.3 M methanol solution of sodium methanethiolate was added dropwise. The mixture was stirred at room temperature for 1 hour. An aqueous solution of ammonium chloride (1 g/5 ml) was added, and the mixture was extracted with 10 ml of ether three times. The extract was washed with 15 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene and methylene chloride) to afford 133 mg (yield 64%) of alpha-(m-benzoylphenyl)-propionitrile as colorless crystals.

Workup

  1. extractionthe mixture was extracted with 10 ml of ether three times
  2. washThe extract was washed with 15 ml of water three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel; benzene and methylene chloride)

Sources & evidence

ORD record
ord-ef3ed11cc192494180d496a11a77c661
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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