3-Chloropropionitrile → 3-(3-Trifluoromethylphenylthio)-propionitrile

HRID 597392

Reaction equation

HRID 597392 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl[CH2:15][CH2:16][C:17]#[N:18]>O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[C:5]([S:9][CH2:15][CH2:16][C:17]#[N:18])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 109633-ChloropropionitrileHCID 14798Sodium HydroxideHCID 1367513-(Trifluoromethyl)benzenethiol

Product 1

HCID 198439363-(3-Trifluoromethylphenylthio)-propionitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 15.9 g (0.09 mol) of 3-trifluoromethylthiophenol and 3.8 g (0.095 mol) of sodium hydroxide pellets in 100 ml of water is heated at 65°-70° C and 8.5 g (0.095 mol) of β-chloropropionitrile are added dropwise whilst stirring. The mixture is heated for a quarter of an hour to the reflux temperature and is then cooled and extracted with ether, and the extract is washed with water and dried with magnesium sulphate. This gives 3-(3-trifluoromethylphenylthio)-propionitrile, which is not isolated.

Workup

  1. temperatureThe mixture is heated for a quarter of an hour to the reflux temperature
  2. temperatureis then cooled
  3. extractionextracted with ether
  4. washthe extract is washed with water
  5. dry with materialdried with magnesium sulphate

Sources & evidence

ORD record
ord-56a53ea130574dc8acfa973d562739c3
Source dataset
uspto-grants-1977_03
Patent number
US04013776

Linked notes

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