Potassium Carbonate → 3-(2-Methyl-1H-imidazol-1-yl)benzonitrile

HRID 1291067Notes

Reaction equation

HRID 1291067 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Br[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12].C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 233813-Bromobenzonitrile

Product 1

HCID 189201913-(2-Methyl-1H-imidazol-1-yl)benzonitrileYield 23.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-methylimidazole (25 g, 0.3 mol) and 3-bromobenzo-nitrile (55 g, 0.3 mol) in pyridine (60 mL) was added K2CO3 (42 g), CuO (1.5 g), Cu powder (1.5 g) and CuBr (1.5 g) under a nitrogen atmosphere. The resulting mixture was heated at reflux temperature for 64 hr. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (10:1) to afford 12.9 g (23%) of 3-(2-methylimidazol-1-yl)benzonitrile as white solids.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature for 64 hr
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (10:1)

Sources & evidence

ORD record
ord-b037bf5d6cb34189bf7620ef22f8c40d
Source dataset
uspto-grants-1998_05
Patent number
US05753682

Reaction notes

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