Sodium borohydride → {1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-yl-methyl]-1H-imidazol-2-yl}-methanol

HRID 1841192Notes

Reaction equation

HRID 1841192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[CH:20]=[O:21])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[CH2:20][OH:21])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86586167HCID 86586167, compound

Product 1

HCID 69043400{1-[1-(3,4-Dichloro-phenyl)-1H-imidazol-4-yl-methyl]-1H-imidazol-2-yl}-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-ylmethyl]-1H-imidazole-2-carbaldehyde (0.52 g, 1.6 mmol) in MeOH (16 ml) was treated with sodium borohydride (0.12 g, 3.2 mmol). The mixture was stirred at rt for 2 h. Then all volatiles were evaporated and the residue was partitioned (AcOEt/H2O). The organic phase was dried (Na2SO4) and concentrated to approximately 30 ml. The title compound was obtained as a white crystalline material (0.21 g, 41%). Mp. 202-203° C. (AcOEt), MS: m/e=322 (M+).

Workup

  1. customThen all volatiles were evaporated
  2. customthe residue was partitioned (AcOEt/H2O)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated to approximately 30 ml

Sources & evidence

ORD record
ord-c9414c19a5604c9a8712e5bc9952553a
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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