p-Chlorothiophenol → 3-[(4-Chlorophenyl)sulfanyl]propanenitrile

HRID 2419846Notes

Reaction equation

HRID 2419846 reaction equation
Cl[CH2:2][CH2:3][C:4]#[N:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][CH:8]=1.[OH-].[Na+]>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH2:2][CH2:3][C:4]#[N:5])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 109633-ChloropropionitrileHCID 14798Sodium Hydroxide

Product 1

HCID 18088053-[(4-Chlorophenyl)sulfanyl]propanenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of β-chloropropionitrile (0.13 mol) are added, whilst stirring at 70°-80° C, to a solution of 17.4 g (0.12 mol) of p-chlorothiophenol and 4.8 g of sodium hydroxide pellets in 50 ml of water. The mixture is kept at 80° C for half an hour. After cooling, it is extracted with ether and the extract is washed with water and dried. 22.5 g of 3-(p-chlorophenylthio)-propionitrile. Melting point = 53-54° C.

Workup

  1. waitThe mixture is kept at 80° C for half an hour
  2. temperatureAfter cooling
  3. extractionit is extracted with ether
  4. washthe extract is washed with water
  5. customdried

Sources & evidence

ORD record
ord-e8fefa89b6a8448ba476d60f771b16df
Source dataset
uspto-grants-1978_08
Patent number
US04107438

Reaction notes

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