Sodium → HCID 14518440, compound

HRID 1723155Notes

Reaction equation

HRID 1723155 reaction equation
[CH3:1][O-].[Na+].[Na].[N:5]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:16]([OH:25])[C:15]=3[CH:26]=2)[CH:9]=[CH:8][N:7]=[CH:6]1>CO>[N:5]1([CH2:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:16]([O:25][CH3:1])[C:15]=3[CH:26]=2)[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 14518438HCID 14518438, compound

Product 1

HCID 14518440HCID 14518440, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred sodium methoxide solution previously prepared starting from 0.46 parts of sodium and 32 parts of methanol were added 6.16 parts of 6-(1H-imidazol-1-ylmethyl)-2-phenyl-1H-benzimidazol-1-ol. After stirring for a while, the whole was concentrated and 2 portions of 18 parts of methylbenzene were added. After evaporation, there were added successively 27 parts of N,N-dimethylformamide and a solution of 2.84 parts of iodomethane in 9 parts of N,N-dimethylformamide. The whole was stirred first for 10 minutes at room temperature and then for 30 minutes at 60° C. The reaction mixture was evaporated and 50 parts of water were added to the residue. The precipitated product was filtered off, washed with water and purified by filtration over silica gel using a mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybisproprane. The product was filtered off and dried, yielding 5.4 parts (88.7%) of 6-(1H-imidazol-1-ylmethyl)-1-methoxy-2-phenyl-1H-benzimidazole; mp. 142.1° C. (compound 227).

Workup

  1. concentrationthe whole was concentrated
  2. addition2 portions of 18 parts of methylbenzene were added
  3. customAfter evaporation, there
  4. additionwere added successively 27 parts of N,N-dimethylformamide
  5. stirringThe whole was stirred first for 10 minutes at room temperature
  6. customThe reaction mixture was evaporated
  7. addition50 parts of water were added to the residue
  8. filtrationThe precipitated product was filtered off
  9. washwashed with water
  10. filtrationpurified by filtration over silica gel using
  11. additiona mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated
  14. customThe residue was crystallized from 2,2'-oxybisproprane
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-fc9001955aa44016a96f1702eed1a5b2
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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