Potassium Cyanide → 3-Methyl-6-(phenylthio)-phenylacetonitrile

HRID 435608Notes

Reaction equation

HRID 435608 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][C:5]1[CH:6]=[C:7]([C:10]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)[CH2:8]Cl>O.C(O)C>[CH3:4][C:5]1[CH:6]=[C:7]([CH2:8][C:1]#[N:2])[C:10]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 125391003-Methyl-6-(phenylthio)-benzyl chloride

Product 1

HCID 125391013-Methyl-6-(phenylthio)-phenylacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

570.7 g of 3-methyl-6-(phenylthio)-benzyl alcohol are dissolved in 1.5 litres of benzene and heated under reflux. There are added dropwise thereto within 45 minutes 352 ml of thionyl chloride and the mixture is boiled for a further 90 minutes. Then the mixture is concentrated under reduced pressure and there is obtained 3-methyl-6-(phenylthio)-benzyl chloride as a red-brown oil. 194 g of potassium cyanide in 250 ml of water are heated under reflux for 17 hours under an argon atmosphere with 616.9 g of 3-methyl-6-(phenylthio)-benzyl chloride in 900 ml of ethanol. Then the ethanol is distilled off under reduced pressure, the residue then diluted with water and extracted with ether. The extracts are washed with water, dried over sodium sulphate and evaporated. There is obtained 3-methyl-6-(phenylthio)-phenylacetonitrile as an oil.

Workup

  1. distillationThen the ethanol is distilled off under reduced pressure
  2. additionthe residue then diluted with water
  3. extractionextracted with ether
  4. washThe extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-2b0640db142e4479a44076773d148632
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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