Sodium Chloride → 2-[2-Methoxy-3-(o-tolylthio)phenyl]acetonitrile

HRID 1164110Notes

Reaction equation

HRID 1164110 reaction equation
[C-:1]#[N:2].[Na+].[CH3:4][O:5][C:6]1[C:11]([CH2:12]Cl)=[CH:10][CH:9]=[CH:8][C:7]=1[S:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.[Cl-].[Na+]>CS(C)=O>[CH3:4][O:5][C:6]1[C:7]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][C:1]#[N:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 20513475o-Tolyl 2-methoxy-3-chloromethylphenyl thioether

Product 1

HCID 205134502-[2-Methoxy-3-(o-tolylthio)phenyl]acetonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Powdered sodium cyanide (1.5 g) was added all at once to a solution of o-tolyl 2-methoxy-3-chloromethylphenyl thioether (8.3 g) in dimethyl sulfoxide (40 ml), and the mixture was stirred for 15 minutes, poured into saturated aqueous solution of sodium chloride and extracted with diethyl ether. The extract was washed with water, dried and then evaporated under reduced pressure to give oily 2-[2-methoxy-3-(o-tolylthio)phenyl]acetonitrile (7.7 g).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ab22cb2c452e459a9e128506dbf3af59
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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