p-Fluoronitrobenzene → 2-Methyl-1-(4-nitrophenyl)-1H-imidazole

HRID 2043379Notes

Reaction equation

HRID 2043379 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:11][C:12]1[N:13]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 9590p-Fluoronitrobenzene2×HCID 10796Cesium carbonateHCID 127492-Methylimidazole

Product 1

HCID 100131182-Methyl-1-(4-nitrophenyl)-1H-imidazoleYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-fluoro-4-nitrobenzene (10 g, 70.9 mmol), 2-methyl-1H-imidazole (5.8 g, 70.9 mmol), and Cs2CO3 (34.7 g, 106.4 mmol) in degassed DMF (200 mL) was heated at 100° C. under nitrogen overnight. When TLC indicated that 1-fluoro-4-nitrobenzene was consumed, the reaction mixture was concentrated in vacuo. The residue was diluted with water (300 mL), and a grey precipitate was formed and was isolated to give 2-methyl-1-(4-nitrophenyl)-1H-imidazole (12.8 g, yield 89%).

Workup

  1. customwas consumed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with water (300 mL)
  4. customa grey precipitate was formed
  5. customwas isolated

Sources & evidence

ORD record
ord-c21efe41e41b429b96cae4472561e3eb
Source dataset
uspto-grants-2013_11
Patent number
US08586624B2

Reaction notes

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