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

HRID 1060508Notes

Reaction equation

HRID 1060508 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-a8a3c381a53a47d5a21ebe2828a2b33b
Source dataset
uspto-grants-2003_02
Patent number
US06524552B2

Reaction notes

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