Imidazole → 2-(1H-imidazol-1-yl)benzonitrile

HRID 619174Notes

Reaction equation

HRID 619174 reaction equation
[OH-].[K+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.F[C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12]>CS(C)=O>[N:3]1([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14797Potassium HydroxideHCID 678552-Fluorobenzonitrile

Product 1

HCID 1902752-(1H-imidazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of KOH (5.81 g) in DMSO (15 mL) was added imidazole (5.0 g, 73.4 mmol). The mixture was stirred for 1 hour, then 2-fluorobenzonitrile (8.76 mL) in DMSO (10 mL) was added dropwise over 20 minutes. The reaction mixture was stirred at room temperature overnight and the product was collected by filtration and washed with water to afford 10.91 g of 2-(1-imidazolyl)benzonitrile as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationthe product was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-007b7681315a49e58271b48efacc8c83
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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