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

HRID 472161

Reaction equation

HRID 472161 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[N:13]=[CH:14][NH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 178418800HCID 178418800, compound

Product 1

HCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazoleYield 48.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

4-fluoronitrobenzene (32.3 g; 0.229 mol) and 4-methyl-1H-imidazole (25 g; 0.3 mol) are mixed at r.t., to this stirred mixture K2CO3 (44 g; 0.3 mol) is added. The reaction mixture is then heated at 120° C. overnight, then cooled at r.t. and poured in water (2 L), the resulting suspension is filtered and washed with water. The obtained solid is dried at 60° C. and recrystallized from ethyl acetate (600 mL), to provide the title compound as a yellow solid (22.5 g; 48.3%). The regioisomer, 4-(5-methyl-1H-imidazol-1yl)nitrobenzene remains in the crystallization mother liquor along with a certain amount of the titled product (TLC: hexane/AcOEt 3:2). C10H9N3O2, MW 203.2.

Workup

  1. additionis added
  2. temperaturecooled at r.t.
  3. filtrationthe resulting suspension is filtered
  4. washwashed with water
  5. customThe obtained solid is dried at 60° C.
  6. customrecrystallized from ethyl acetate (600 mL)

Sources & evidence

ORD record
ord-467395d666b0426ab2aad45f8362ca2e
Source dataset
uspto-grants-2014_01
Patent number
US08633208B2

Linked notes

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