Sodium Cyanide → HCID 12232352, compound

HRID 435701Notes

Reaction equation

HRID 435701 reaction equation
[C-:1]#[N:2].[Na+].[F: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>CS(C)=O>[F: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

4

Reactant 2

HCID 8929Sodium CyanideHCID 12232349HCID 12232349, compound

Product 1

HCID 12232352HCID 12232352, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

18.6 g of sodium cyanide in 222 ml of dimethyl sulphoxide are treated at 50° C with 74 g of 3-fluoro-6-(phenylthio)-benzyl chloride in 75 ml of dimethyl sulphoxide in one portion. The resulting dark solution is stirred at 45°-50° C for 1 hour, subsequently poured on to 1500 ml of ice-water and extracted with ether. The organic phase is washed three times with 500 ml of water each time, dried over sodium sulphate and evaporated. There is obtained 3-fluoro-6-(phenylthio)-phenylacetonitrile as a reddish oil.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed three times with 500 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-c3ddf21f310245efb94e33ec4295c55b
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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