Imidazole → HCID 17163622, compound

HRID 1284486Notes

Reaction equation

HRID 1284486 reaction equation
Cl[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>C(O)C>[N:12]1([CH2:2][C:3]2[NH:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 17163622HCID 17163622, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloromethyl-1H-benzimidazole (4.85 g) and imidazole (9.9 g) in ethanol (37 ml) was stirred at 70° C. for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (120 g) with a mixture of methanol and dichloromethane (5:95) as an eluent to afford an oil, which was crystallized from ethyl acetate. Recrystallization from a mixture of methanol and diethyl ether to give 2-(imidazol-1-yl)methyl-1H-benzimidazole (0.76 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (120 g) with a mixture of methanol and dichloromethane (5:95) as an eluent
  3. customto afford an oil, which
  4. customwas crystallized from ethyl acetate
  5. customRecrystallization
  6. additionfrom a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-54ca20e53838477eab822a359595581f
Source dataset
uspto-grants-1986_01
Patent number
US04563455

Reaction notes

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