Ammonium Chloride → 2-(3-Phenoxyphenyl)propanenitrile

HRID 1759434Notes

Reaction equation

HRID 1759434 reaction equation
CS[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][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>[O:13]([C:9]1[CH:8]=[C:7]([CH:3]([CH3:6])[C:4]#[N:5])[CH:12]=[CH:11][CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 54570589alpha-(Methylthio)-alpha-(m-phenoxyphenyl)propionitrile

Product 1

HCID 1180062-(3-Phenoxyphenyl)propanenitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

451 mg of alpha-(methylthio)-alpha-(m-phenoxyphenyl)propionitrile was dissolved in 1 ml of anhydrous methanol, and 1.1 ml of a 2.3 M methanol solution of sodium methanethiolate was added. The mixture was stirred at room temperature for 2 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 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; hexane and methylene chloride) to afford 316 mg (yield 83%) of alpha-(m-phenoxyphenyl)-propionitrile as a colorless oil.

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; hexane and methylene chloride)

Sources & evidence

ORD record
ord-8967a194c26d489bb2a33a8c55e08eee
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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