Imidazole → 2-Methyl-1-(4-nitro-2-(trifluoromethyl)phenyl)-1H-imidazole

HRID 1968419Notes

Reaction equation

HRID 1968419 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19].[C:22]([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:22][C:2]1[N:1]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 598224512-Methyl-1-(4-nitro-2-(trifluoromethyl)phenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of imidazole (2.20 g, 26.8 mmol) in 20 mL DMF at 0° C. under argon atmosphere is added with sodium hydride (60% dispersion in mineral oil, 1.43 g, 35.7 mmol) potion wise. After 15 min, 1-Fluoro-4-nitro-2-trifluoromethyl-benzene (5.0 g, 23.9 mmol) is added. The resulting reaction mixture is allowed to warm to room temperature and kept stirring for 2 hr. Then the reaction mixture is poured into 100 mL saturated NaHCO3 solution, extracted three times with 150 mL ethyl acetate. The organic extracts are washed with brine, and dried over MgSO4. Filtration and concentration under reduced pressure, afforded the title compound as white powder, which is directly used for the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted three times with 150 mL ethyl acetate
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-35d6986f56634d6cacd0a4876a78e256
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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