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

HRID 2419847Notes

Reaction equation

HRID 2419847 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-0ebb508a01024f4894677c2e2abae37a
Source dataset
uspto-grants-1978_08
Patent number
US04107438

Reaction notes

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