Benzyl Chloride → HCID 20026628, compound

HRID 1723157Notes

Reaction equation

HRID 1723157 reaction equation
[N:1]1([CH2:6][C:7]2[CH:22]=[CH:21][C:10]3[N:11]([OH:20])[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].Cl[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[N:1]1([CH2:6][C:7]2[CH:22]=[CH:21][C:10]3[N:11]([O:20][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 14518515HCID 14518515, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20026628HCID 20026628, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3 parts of 5-(1H-imidazol-1-ylmethyl)-2-phenyl-1H-benzimidazol-1-ol and 47 parts of N,N-dimethylformamide was stirred till a clear solution was obtained. 0.5 Parts of a sodium hydride dispersion 50% were added portionwise and stirring was continued till hydrogen evolution had ceased. Upon complete addition, 1.2 parts of (chloromethyl)benzene were added at once at room temperature. Upon complete reaction, the N,N-dimethylformamide layer was evaporated. The residue was taken up in water and the product was extracted with methylbenzene and a mixture of trichloromethane and methanol (90:10 by volume). The combined extracts were dried, filtered and 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 a small amount of ethyl acetate and 2,2'-oxybispropane and dried in vacuo at 50° C., yielding 2.64 parts (66.7%) of 5-(1H-imidazol-1-ylmethyl)-2-phenyl-1-(phenylmethoxy)-1H-benzimidazole; (compound 253).

Workup

  1. customwas obtained
  2. stirringstirring
  3. additionwere added at once at room temperature
  4. customUpon complete reaction
  5. customthe N,N-dimethylformamide layer was evaporated
  6. extractionthe product was extracted with methylbenzene
  7. additiona mixture of trichloromethane and methanol (90:10 by volume)
  8. customThe combined extracts were dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from ethyl acetate
  16. filtrationThe product was filtered off
  17. washwashed with a small amount of ethyl acetate and 2,2'-oxybispropane
  18. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-f627c3b5672540488d8d84235c0a95fc
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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