Chloroacetonitrile → [(3,4-Dichlorophenyl)sulfanyl]acetonitrile

HRID 1680057Notes

Reaction equation

HRID 1680057 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].Cl[CH2:13][C:14]#[N:15]>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:13][C:14]#[N:15])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 14798Sodium HydroxideHCID 799643,4-Dichlorobenzenethiol2×

Product 1

HCID 18542995[(3,4-Dichlorophenyl)sulfanyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.9 g (0.10 mol) of 3,4-dichlorobenzenethiol are mixed in the cold with a solution of 4.1 g of sodium hydroxide (about 0.1 mol) in 50 ml of water. The mixture is heated to 60°-70° C. and 7.5 ml (0.12 mol; 20% excess relative to the 3,4-dichlorobenzenethiol) of chloroacetonitrile are added dropwise. The whole is then heated under reflux for about 30 minutes and cooled, the oil which has formed is extracted with ether, the ether solution is washed with dilute sodium hydroxide solution and water, until the pH of the wash waters is neutral, and dried over SO4Mg, the SO4Mg is filtered off, the ether is evaporated off and the expected nitrile, which is in the form of a chromatographically pure oil, is collected.

Workup

  1. temperatureThe mixture is heated to 60°-70° C.
  2. temperatureThe whole is then heated
  3. temperatureunder reflux for about 30 minutes
  4. temperaturecooled
  5. customthe oil which has formed
  6. extractionis extracted with ether
  7. washthe ether solution is washed with dilute sodium hydroxide solution and water, until the pH of the wash waters
  8. customdried over SO4Mg, the SO4Mg
  9. filtrationis filtered off
  10. customthe ether is evaporated off
  11. customis collected

Sources & evidence

ORD record
ord-837cb09b4ae54e5ea14ff08ca4b47179
Source dataset
uspto-grants-1981_06
Patent number
US04271194

Reaction notes

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