Sodium Cyanide → 4-(Trifluoromethylthio)phenylacetonitrile

HRID 1995676Notes

Reaction equation

HRID 1995676 reaction equation
[C-:1]#[N:2].[Na+].[F:4][C:5]([S:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)([F:7])[F:6]>O.[Cl-].C([N+](CC)(CC)CC)C>[F:4][C:5]([S:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][C:1]#[N:2])=[CH:11][CH:10]=1)([F:7])[F:6]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 27831641-(Chloromethyl)-4-((trifluoromethyl)sulfanyl)benzene

Product 1

HCID 27779054-(Trifluoromethylthio)phenylacetonitrileYield 123.3%

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

75 g of sodium cyanide were dissolved in 200 ml of water, and 15 g of tetraethylammonium chloride after 450 g of 4-trifluoromethylmercapto-benzyl chloride were added. The reaction mixture was stirred at 110° C. for 1 hour and then cooled. The cold mixture was diluted with 200 ml of water and then extracted twice with methylene chloride. After drying the organic phase, the solvent was distilled off and the crude product was purified by distillation. 410 g of 4-trifluoromethylmercapto-benzyl cyanide were obtained. Boiling point=95°-97° C./1.5 mm Hg; nD20 =1.5025.

Workup

  1. temperaturecooled
  2. extractionextracted twice with methylene chloride
  3. customAfter drying the organic phase
  4. distillationthe solvent was distilled off
  5. distillationthe crude product was purified by distillation

Sources & evidence

ORD record
ord-04e50a6e59354db9bcbbbdc7529d2acc
Source dataset
uspto-grants-1983_09
Patent number
US04405639

Reaction notes

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