Imidazole → HCID 178420757, compound

HRID 1723158Notes

Reaction equation

HRID 1723158 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[CH:15][C:9]=2[N:8]=1>C(O)C.C(=O)([O-])[O-].[K+].[K+]>[N:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][C:14]([CH2:16][N:17]4[CH:21]=[CH:20][N:19]=[CH:18]4)=[CH:15][C:9]=3[N:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 178478313HCID 178478313, compound

Product 1

HCID 178420757HCID 178420757, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 4.4 parts of 1H-imidazole and 5 parts of 2-chloro-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole was molten together for 1 hour at 140° C. The sticky mixture was taken up in a mixture of ethanol and potassium carbonate. The supernatant liquid was decanted and evaporated to dry. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in 15 parts of water. The product was filtered off and crystallized from a mixture of methanol and ethyl acetate, yielding 0.95 parts (17%) of 2-(1H-imidazol-1-yl)-5-(1H-imidazol-1-ylmethyl)-1H-benzimidazole; mp. 226.2° C. (compound 258).

Workup

  1. customThe supernatant liquid was decanted
  2. customevaporated
  3. customto dry
  4. customThe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:10:0.1 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. filtrationThe product was filtered off
  9. customcrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-ef69b435e2f84a5a8311f0333897d742
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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