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

HRID 365742Notes

Reaction equation

HRID 365742 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Na].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>C(#N)C>[N:11]1([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 678552-FluorobenzonitrileHCID 5360545Sodium

Product 1

HCID 1902752-(1H-imidazol-1-yl)benzonitrileYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

2-Fluorobenzonitrile (0.70 g, 5.78 mmol) was dissolved in acetonitrile (1 ml), and a sodium salt of imidazole (1.34 g, 14.8 mmol) was added thereto, followed by stirring at 100° C. for 1.5 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (the sample was eluted with an increasing concentration of chloroform from chloroform/hexane=1/2 to 100% chloroform) to give the title compound (0.96 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (the sample
  3. washwas eluted with an increasing concentration of chloroform from chloroform/hexane=1/2 to 100% chloroform)

Sources & evidence

ORD record
ord-83d0feb8411e47b0ab83f7e6b68cad00
Source dataset
uspto-grants-2000_10
Patent number
US06127541

Reaction notes

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