Water → 2-Phenylthio-5-trifluoromethyl-phenylacetonitrile

HRID 435719Notes

Reaction equation

HRID 435719 reaction equation
[C-:1]#[N:2].[Na+].[C:4]1([S:10][C:11]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:12]=2[CH2:13]Cl)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CS(C)=O>[C:4]1([S:10][C:11]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:12]=2[CH2:13][C:1]#[N:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 15619001HCID 15619001, compound

Product 1

HCID 122239582-Phenylthio-5-trifluoromethyl-phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
40 °C

Procedure

11.2 g of sodium cyanide in 135 ml of dimethyl sulphoxide are warmed to 40° C and treated dropwise over a period of 10 minutes with a solution of 87 g of 2-(phenylthio)-5-trifluoromethyl-benzyl chloride in 72 ml of dimethyl sulphoxide. The mixture is stirred at 40° C for 9 hours, cooled to room temperature, treated with 200 ml of water and extracted with 200 ml of ether. The aqueous phase is then extracted twice with 100 ml of ether each time. The combined organic phases are now washed twice with 200 ml of water each time, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 2-(phenylthio)-5-trifluoromethyl-phenylacetonitrile as a dark-red oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with 200 ml of ether
  3. extractionThe aqueous phase is then extracted twice with 100 ml of ether each time
  4. washThe combined organic phases are now washed twice with 200 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-105d5a670a594d90a13aeec25e978688
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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