Imidazole → 5-Amino-4-fluoro-2-(1-imidazolyl)nitrobenzene

HRID 1954021Notes

Reaction equation

HRID 1954021 reaction equation
[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[H-].[Na+]>O>[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 27583122,4-Difluoro-5-nitroaniline

Product 1

HCID 232958215-Amino-4-fluoro-2-(1-imidazolyl)nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12 g (0.068 mol) of 5-amino-2,4-difluoronitrobenzene were slowly added at 0° C. to a solution of 4.7 g of imidazole (0.069 mol) and 2.1 g of sodium hydride (80% in oil; 0.07 mol) and then stirred at this temperature for several hours. The mixture was then diluted with water and extracted several times with methylene chloride. The residue after drying and evaporation was recrystallized from isopropanol.

Workup

  1. extractionextracted several times with methylene chloride
  2. customThe residue after drying
  3. customevaporation
  4. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-ae16d0c9eb5d41978167ef239ba9d959
Source dataset
uspto-grants-2000_09
Patent number
US06121265

Reaction notes

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