Ammonium Chloride → 2-(3-Benzoylphenyl)propanenitrile

HRID 1759436Notes

Reaction equation

HRID 1759436 reaction equation
CS[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)([CH3:6])[C:4]#[N:5].C[S-].[Na+].[Cl-].[NH4+]>CO>[C:13]([C:9]1[CH:8]=[C:7]([CH:3]([CH3:6])[C:4]#[N:5])[CH:12]=[CH:11][CH:10]=1)(=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 12677424HCID 12677424, compound

Product 1

HCID 393252-(3-Benzoylphenyl)propanenitrileYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

241 mg of alpha-(methylthio)-alpha-(m-benzoylphenyl)propionitrile was dissolved in 1 ml of methanol, and 0.60 ml of a 2.3 M methanol solution of sodium methanethiolate was added dropwise. The mixture was stirred at room temperature for 1.5 hours. An aqueous solution of ammonium chloride (2 g/10 ml) was added, and the mixture was extracted with 10 ml of ether three times. The extract was washed with 20 ml of water three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; methylene chloride) to afford 167 mg (yield 79%) of alpha-(m-benzoylphenyl)propionitrile.

Workup

  1. extractionthe mixture was extracted with 10 ml of ether three times
  2. washThe extract was washed with 20 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; methylene chloride)

Sources & evidence

ORD record
ord-269a592a071e427db5b1c5a08fd59b04
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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