Benzonitrile → 1-Methyl-4-phenyl-5-(4-pyridyl)imidazole

HRID 479775Notes

Reaction equation

HRID 479775 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][N:14]([CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[CH:15]=O.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[CH3:13][N:14]1[C:17]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:31]=[CH:15]1

Participants

6

Reactant 4

HCID 7505BenzonitrileHCID 7912DiisopropylamineHCID 15893405N-Methyl-N-[4-picolyl]formamideHCID 178418339Butyllithium

Product 1

HCID 187714831-Methyl-4-phenyl-5-(4-pyridyl)imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of di-iso-propyl-amine (11.2 mL, 79.9 mmol ) in 150 mL of THF at −78° C. was added n-butyllithium (31.9 mL of 2.5 M solution, 79.9 mmol). To the resulting mixture was added a solution of N-methyl-N-[4-picolyl]formamide (10 g, 66.5 mmol) in THF. The resulting orange-brown solution was stirred at −78° C. for 20 min, at which time benzonitrile (13.6 mL, 133 mmol) was added. The resulting dark brown mixture was allowed to warm to rt and stirred for 1 h, heated to reflux for 4 h, and then cooled to rt and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a light tan solid (5.83 g, 37%): mp 158-159° C.

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureto reflux for 4 h
  4. temperaturecooled to rt
  5. custompartitioned between CH2Cl2 and H2O
  6. extractionThe organic extract
  7. washwas washed with aqueous NaCl
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed in vacuo
  10. customthe residue was purified by flash chromatography
  11. washeluting with 50:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-addb017f656140f19476d3e779c6854d
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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