Water → 2-(4-(Methylthio)phenyl)acetonitrile

HRID 413469Notes

Reaction equation

HRID 413469 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[C-:11]#[N:12].[Na+].O>C1(C)C=CC=CC=1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:11]#[N:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 8929Sodium CyanideHCID 701281-(Chloromethyl)-4-(methylthio)benzene

Product 1

HCID 27600872-(4-(Methylthio)phenyl)acetonitrileYield 100.5%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
82.5 °C

Procedure

Under an atmosphere of nitrogen, 25.9 g (150 mmol) of 4-(methylthio)benzyl chloride were dissolved in 45.5 g of toluene. 9.29 g (180 mmol) of sodium cyanide, 0.92 g (2.9 mmol) of tetrabutylammonium chloride and 14.4 g of water were then added. The mixture was stirred at 80-85° C. for 2 h. The reaction mixture was admixed with 30 g of toluene and 45 g of water, the aqueous phase was decanted off and the organic phase was concentrated. This gave a residue of 24.6 g of the title product in a yield of >95% (according to NMR) in the form of a pink solid.

Workup

  1. customthe aqueous phase was decanted off
  2. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-44234c8b14c946808dc1891483781d6a
Source dataset
uspto-grants-2003_05
Patent number
US06566527B1

Reaction notes

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