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

HRID 1756520Notes

Reaction equation

HRID 1756520 reaction equation
Cl[CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>C(#N)C>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

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

To a stirred solution of 88.7 parts of 1-[chlorophenylmethyl]-4-nitrobenzene in 790 parts of acetonitrile were added 121.8 parts of 1H-imidazole. After stirring for 24 hours at reflux temperature, the reaction mixture was evaporated. The residue was taken up in methylbenzene. This solution was washed with K2CO3 (aq.), dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 53 parts (53%) of 1-[(4-nitrophenyl)phenylmethyl]-1H-imidazole (interm. 42).

Workup

  1. temperatureat reflux temperature
  2. customthe reaction mixture was evaporated
  3. washThis solution was washed with K2CO3 (aq.)
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  8. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-5e1bbb8d08d7427e82d2dd37fd50a945
Source dataset
uspto-grants-1995_08
Patent number
US05441954

Reaction notes

Loading…