4-Toluenesulfonyl chloride → HCID 22033501, compound

HRID 325040Notes

Reaction equation

HRID 325040 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-3f6764e44bca497ab365e533aa46a9c8
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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