Water → 4-n-butylthio-benzonitrile

HRID 394849Notes

Reaction equation

HRID 394849 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([SH:20])[CH2:17][CH2:18][CH3:19].O>CC(N(C)C)=O>[CH2:16]([S:20][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8012ButanethiolHCID 11430Potassium CarbonateHCID 121634-Chlorobenzonitrile

Product 1

HCID 110196724-n-butylthio-benzonitrile

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a well-stirred suspension of 41.27 g (0.3 mol) of 4-chlorobenzonitrile, 58.05 g (0.42 mol) of potassium carbonate and 200 ml DMA a solution of 27.06 g (0.3 mol) of 1-butanethiol in 50 ml of DMA are added under an atmosphere of nitrogen. The resulting mixture is heated to 80° C. and stirred at this temperature for 24 hours. Then, the reaction mixture is cooled to room temperature and poured into 750 ml of water. The crude product is extracted with 300 ml of ethyl acetate, washed with water, dried over MgSO4. Thereafter, ethyl acetate is removed. Then, fractional distillation yields 52.88 9 (80.4%) of colorless liquid 4-n-butylthio-benzonitrile.

Workup

  1. additionare added under an atmosphere of nitrogen
  2. temperatureThen, the reaction mixture is cooled to room temperature
  3. extractionThe crude product is extracted with 300 ml of ethyl acetate
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customThereafter, ethyl acetate is removed
  7. distillationThen, fractional distillation

Sources & evidence

ORD record
ord-d9f3e3f65d3948caaf50f5962f521157
Source dataset
uspto-grants-2003_08
Patent number
US06603020B1

Reaction notes

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