Sodium Iodide → 2-[2-Methoxy-3-(2-chlorophenylthio)phenyl]acetonitrile

HRID 1164081Notes

Reaction equation

HRID 1164081 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9]Cl)=[CH:7][CH:6]=[CH:5][C:4]=1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18].[I-].[Na+].[C-:21]#[N:22].[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[C:4]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:5][CH:6]=[CH:7][C:8]=1[CH2:9][C:21]#[N:22]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 205134642-Chlorophenyl 2-methoxy-3-chloromethylphenyl thioether

Product 1

HCID 205134652-[2-Methoxy-3-(2-chlorophenylthio)phenyl]acetonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-chlorophenyl 2-methoxy-3-chloromethylphenyl thioether (9.2 g) and sodium iodide (4.8 g) in dimethyl sulfoxide (50 ml) was stirred at room temperature. To the mixture was added powdered potassium cyanide (2.1 g) all at once, and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was poured into ice-water and extracted with diethyl ether. The extract was washed with water, dried and then evaporated to give oily 2-[2-methoxy-3-(2-chlorophenylthio)phenyl]acetonitrile (8.9 g). This product was purified by column chromatography (silica gel 150 g, benzene) to give purified oily product (4.1 g).

Workup

  1. stirringwas stirred at 70° C. for 3 hours
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-ebd4cf41353b463da36c5bcd7b307108
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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