4-Toluenesulfonyl chloride → HCID 22033501, compound

HRID 1791861Notes

Reaction equation

HRID 1791861 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1)#[N:2].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 28008154-(2-Hydroxyethyl)benzonitrile2×

Product 1

HCID 22033501HCID 22033501, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Cyanophenyl)ethanol (1.46 g; 9.9 mmol) and 4-toluenesulfonyl chloride (1.9 g; 10 mmol) were stirred in pyridine (20 mL) at 5° C. for 3 hours. Work-up was performed by removing the solvent, addition of 2M aqueous HCl and extraction with EtOAc. The organic phase was washed with aqueous citric acid, then passed through a short plug of silica gel with Et2O. Removal of the solvent in vacuo afforded a colourless oil, containing ca. 30% of unreacted 2-(4-cyanophenyl)ethanol according to 1H NMR. The oil was further subjected to the reaction conditions above for 2 hours. Work-up as above afforded 2.0 g (66%) of the sub-title compound as a yellow solid.

Workup

  1. customby removing
  2. additionthe solvent, addition of 2M aqueous HCl and extraction with EtOAc
  3. washThe organic phase was washed with aqueous citric acid
  4. customRemoval of the solvent in vacuo
  5. customafforded a colourless oil
  6. customThe oil was further subjected to the reaction conditions above for 2 hours

Sources & evidence

ORD record
ord-737deac25e6e41d4beb1f59e139c081e
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

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