Imidazole → 2-(imidazol-1-yl)methyl-1-phenyl-1H-benzimidazole

HRID 1284485Notes

Reaction equation

HRID 1284485 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>C(O)C.O>[N:18]1([CH2:2][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[N:4]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazole

Product 1

HCID 202518882-(imidazol-1-yl)methyl-1-phenyl-1H-benzimidazoleYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-chloromethyl-1-phenyl-1H-benzimidazole (3.4 g) and imidazole (4.8 g) in ethanol (25 ml) was stirred at 60° C for 7 hours. The reaction mixture was concentrated under reduced pressure to give an oil, which was diluted with water and extracted three times with dichloromethane. The combined extract was washed twice with water and once with brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (100 g) with a mixture of methanol and dichloromethane (3:97) as an eluent to afford an oil, which was crystallized from a mixture of ethyl acetate and hexane to give 2-(imidazol-1-yl)methyl-1-phenyl-1H-benzimidazole (2.65 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give an oil, which
  3. extractionextracted three times with dichloromethane
  4. extractionThe combined extract
  5. washwas washed twice with water and once with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (100 g) with a mixture of methanol and dichloromethane (3:97) as an eluent
  9. customto afford an oil, which
  10. customwas crystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-e54b37a4bbdb47e48634ded687ad68eb
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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