Dimethyl Sulfoxide → Benzonitrile, p-imidazol-1-yl-

HRID 619145Notes

Reaction equation

HRID 619145 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].CS(C)=O.F[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1>O>[N:1]1([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 135744Benzonitrile, p-imidazol-1-yl-Yield 31.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of imidazole (5.13 g, 75.35 mmol), K2CO3 (11.45 g) and DMSO (50 ml) at room temperature was added to 4-fluorobenzonitrile (10.04 g) in one portion. The reaction mixture was stirred at room temperature for 1 hour, and then was warmed on a steam for 2 hours. The reaction mixture was cooled to room temperature, and poured into cold water. A precipitate formed which was collected by filtration and washed with water and recrystallized from CHCl3 /hexane to afford 4.07 g of 4-(1-imidazolyl)benzonitrile, m.p. 146-148° C.

Workup

  1. temperaturewas warmed on a steam for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customA precipitate formed which
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customrecrystallized from CHCl3 /hexane

Sources & evidence

ORD record
ord-7c46a3466f0b4763bd83429268f8a890
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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