Sodium Chloride → [4-(Phenylsulfanyl)phenyl]acetonitrile

HRID 621638Notes

Reaction equation

HRID 621638 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[C-:16]#[N:17].[Na+].[Cl-].[Na+]>>[C:16]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)#[N:17]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 710221-(Chloromethyl)-4-(phenylthio)benzene

Product 1

HCID 238605[4-(Phenylsulfanyl)phenyl]acetonitrileYield 100.7%

Procedure

The 1-chloromethyl-4-phenylthiobenzene (3.0 g) is dissolved in N,N-dimemthylformamide (15 ml), and thereto is added finely divided sodium cyanide (1.0 g), and the mixture is stirred at room temperature for 17 hours. To the reaction mixture are added saturated aqueous sodium chloride solution (50 ml) and ice water (50 ml), and the mixture is extracted with ethyl acetate (100 ml×3). The combined extracts are washed with saturated aqueous sodium chloride solution (50 ml×3), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1-cyanomethyl-4-phenylthiobenzene (2.9 g).

Workup

  1. extractionthe mixture is extracted with ethyl acetate (100 ml×3)
  2. washThe combined extracts are washed with saturated aqueous sodium chloride solution (50 ml×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-369e39a2172b42238e3a4dac89f46441
Source dataset
uspto-grants-1989_04
Patent number
US04824834

Reaction notes

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