Imidazole → HCID 14518416, compound

HRID 1723132Notes

Reaction equation

HRID 1723132 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.Cl[CH2:8][C:9]1[CH:20]=[CH:19][C:12]2[N:13]([CH3:18])[C:14]([CH2:16][CH3:17])=[N:15][C:11]=2[CH:10]=1>C(#N)C>[CH2:16]([C:14]1[N:13]([CH3:18])[C:12]2[CH:19]=[CH:20][C:9]([CH2:8][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:10][C:11]=2[N:15]=1)[CH3:17]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 14518406HCID 14518406, compound

Product 1

HCID 14518416HCID 14518416, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6.8 parts of 1H-imidazole, 4.9 parts of 5-(chloromethyl)-2-ethyl-1-methyl-1H-benzimidazole monohydrochloride and 80 parts of acetonitrile was stirred and refluxed for 3 hours. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from ethyl acetate. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 2.6 parts (54%) of 2-ethyl-5-(1H-imidazol-1-yl-methyl)-1-methyl-1H-benzimidazole; mp. 127.3° C. (compound 1).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from ethyl acetate
  8. filtrationThe product was filtered off
  9. washwashed with 2,2'-oxybispropane
  10. customdried

Sources & evidence

ORD record
ord-ca3003da746947ecbf2a288dfc12b1f9
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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