Imidazole → 1-[(4-Nitrophenyl)(phenyl)methyl]-1H-imidazole

HRID 1739811Notes

Reaction equation

HRID 1739811 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[CH:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1>C(#N)C>[N+:14]([C:11]1[CH:10]=[CH:9][C:8]([CH:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:13][CH:12]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 135417341-[Chloro(phenyl)methyl]-4-nitrobenzene

Product 1

HCID 141740671-[(4-Nitrophenyl)(phenyl)methyl]-1H-imidazoleYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Imidazole (121.8 g) was added to a mixture of 1-(chlorophenylmethyl)-4-nitrobenzene (88.7 g) in ACN (1000 ml) and the reaction mixture was stirred and refluxed for 24 hours. The solvent was evaporated. The residue was dissolved in toluene, washed with a 10% K2CO3 solution, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 53 g (53%) of 1-[(4-nitrophenyl)phenylmethyl]-1H-imidazole (interm. 1-a).

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in toluene
  4. washwashed with a 10% K2CO3 solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a4ab3bb76ab2487ea150013bea4ec9da
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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