Sodium borohydride → (1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazol-5-yl)methanol

HRID 1385810Notes

Reaction equation

HRID 1385810 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C:14]([CH:15]=[O:16])=[C:13]([Cl:17])[N:12]=[C:11]1[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[C:14]([CH2:15][OH:16])=[C:13]([Cl:17])[N:12]=[C:11]1[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 150885051-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazole-5-carbaldehyde

Product 1

HCID 15088539(1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.1 g, 29 mmole) was added in three portions to a stirred mixture of crude 1-benzyl-4-chloro-5-formyl-2-(4-nitrophenyl)imidazole (54.2 g, 88 mmole) in methanol (250 ml) at room temperature. After two hours, more sodium borohydride (0.51 g, 15 mmol) was added, the mixture was stirred for 30 minutes and the methanol was evaporated. The residue was mixed with water (250 ml) and extracted with methylene chloride (200 ml, 3×50 ml). The combined organic solutions were washed with water (2×50 ml) and dried (NaSO4) overnight.

Workup

  1. customthe methanol was evaporated
  2. additionThe residue was mixed with water (250 ml)
  3. extractionextracted with methylene chloride (200 ml, 3×50 ml)
  4. washThe combined organic solutions were washed with water (2×50 ml)
  5. dry with materialdried (NaSO4) overnight

Sources & evidence

ORD record
ord-7c83911ee7f5485da0c5623d9d2acdf2
Source dataset
uspto-grants-2001_07
Patent number
US06264914B1

Reaction notes

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