Sodium Cyanide → 4-(Trifluoromethylthio)phenylacetonitrile

HRID 2050090Notes

Reaction equation

HRID 2050090 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1>CS(C)=O>[F:14][C:13]([F:16])([F:15])[S:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:1]#[N:2])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 27778824-(Trifluoromethylthio)benzyl bromide

Product 1

HCID 27779054-(Trifluoromethylthio)phenylacetonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (3.9 g, 0.08 mol) is added to 40 ml of dimethylsulfoxide at 65° C. under N2. The heat is removed and α-bromo-4-trifluoromethylthiotoluene (14.3 g real, 0.053 mol) is added dropwise at such a rate that the exotherm never raises the temperature above 75° C. The red-colored reaction is heated to 90°-95° C. for about 45 minutes, then cooled to room temperature and treated with 50-100 ml of ice water. The aqueous suspension is extracted with several portions of ether which are combined, washed with water, and dried over sodium sulfate. Evaporation in vacuo gives 9.7 g of a dark red oil 95% pure by glc.

Workup

  1. customThe heat is removed
  2. temperaturenever raises the temperature above 75° C
  3. customThe red-colored reaction
  4. temperatureis heated to 90°-95° C. for about 45 minutes
  5. extractionThe aqueous suspension is extracted with several portions of ether which
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-849812209c4045edb7099924cb2d6e01
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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