Hydrochloric Acid → 6-[(1H-imidazol-1-yl)phenylmethyl]-2-methyl-1H-benzimidazol-1-ol

HRID 1723151Notes

Reaction equation

HRID 1723151 reaction equation
[N:1]1([CH:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH3:15])=[C:9]([N+:17]([O-:19])=O)[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.CC(O)C.Cl.[H][H]>CO>[N:1]1([CH:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:12]=[CH:11][C:10]3[N:13]=[C:14]([CH3:15])[N:17]([OH:19])[C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 53740391HCID 53740391, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 538738956-[(1H-imidazol-1-yl)phenylmethyl]-2-methyl-1H-benzimidazol-1-olYield 40.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.9 parts of N-[4-[(1H-imidazol-1-yl)phenylmethyl]-2-nitrophenyl]acetamide, 12 parts of 2-propanol, saturated with hydrogen chloride and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of platinium-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in dichloromethane and water and then the solution was neutralized with an ammonium hydroxide solution. The dichloromethane layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (85:15 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 2.2 parts (40.6%) of 6-[(1H-imidazol-1-yl)phenylmethyl]-2-methyl-1H-benzimidazol-1-ol as a residue (compound 219).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customThe dichloromethane layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (85:15 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d9d26779372d48e8bbeb985455c85891
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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