Sodium borohydride → HCID 14518421, compound

HRID 1723105Notes

Reaction equation

HRID 1723105 reaction equation
[CH3:1][O: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].[BH4-].[Na+]>CO>[CH3:1][O:2][N:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[OH:13])=[CH:11][C:6]=2[N:5]=[C:4]1[CH3:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14518420HCID 14518420, compound

Product 1

HCID 14518421HCID 14518421, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(a-4) To a stirred solution of 3.4 parts of (1-methoxy-2-methyl-1H-benzimidazol-5-yl) phenylmethanone in 64 parts of methanol were added 0.6 parts of sodium tetrahydroborate. After stirring for 30 minutes at room temperature, the methanol layer was evaporated. Water was added to the residue and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 45 parts of ethyl acetate. The product was filtered off and dried, yielding 2.8 parts (80%) of 1-methoxy-2-methyl-α-phenyl-1H-benzimidazole-5-methanol (int. 51).

Workup

  1. customthe methanol layer was evaporated
  2. additionWater was added to the residue
  3. extractionthe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from 45 parts of ethyl acetate
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-82c77c54cd4f472194f5dfbbd80a87bb
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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