Methanol → HCID 14518420, compound

HRID 1723104Notes

Reaction equation

HRID 1723104 reaction equation
Cl.[OH:2][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:13])=[CH:11][C:6]=2[N:5]=[C:4]1[CH3:20].[Na].[CH3:22]O>>[CH3:22][O:2][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:11][C:6]=2[N:5]=[C:4]1[CH3:20]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 14518419HCID 14518419, compound

Product 1

HCID 14518420HCID 14518420, compoundYield 60%

Procedure

(a-3) 11.55 Parts of (1-hydroxy-2-methyl-1H-benzimidazol-5-yl) phenyl methanone monohydrochloride were added to a stirred solution of 1.84 parts of sodium in 80 parts of methanol. After stirring for 15 minutes at room temperature, the solvent was evaporated and the residue was taken up in methylbenzene. After evaporation, the residue was dissolved in 54 parts of N,N-dimethylformamide and 6.24 parts of iodomethane were added. The reaction mixture was stirred for 2 hours at room temperature. The N,N-dimethylformamide layer was evaporated in vacuo. The residue was taken up in water and the product was extracted with methylbenzene. The extract was dried, filtered and evaporated. The residue was washed with 2,2'-oxybispropane, yielding 6.4 parts (60.0%) of (1-methoxy-2-methyl-1H-benzimidazol-5-yl) phenylmethanone; mp. 67.7° C. (int. 50).

Workup

  1. customthe solvent was evaporated
  2. customAfter evaporation
  3. dissolutionthe residue was dissolved in 54 parts of N,N-dimethylformamide and 6.24 parts of iodomethane
  4. additionwere added
  5. stirringThe reaction mixture was stirred for 2 hours at room temperature
  6. customThe N,N-dimethylformamide layer was evaporated in vacuo
  7. extractionthe product was extracted with methylbenzene
  8. customThe extract was dried
  9. filtrationfiltered
  10. customevaporated
  11. washThe residue was washed with 2,2'-oxybispropane

Sources & evidence

ORD record
ord-0c40e0763c0d46568b22801c633f1d1a
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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