Water → 2-Methyl-1-(4-nitrophenyl)-1H-imidazole

HRID 487992Notes

Reaction equation

HRID 487992 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.O>CN(C=O)C.C(OCC)(=O)C>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[CH3:3])=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 127492-MethylimidazoleHCID 24758Sodium hydride

Product 1

HCID 100131182-Methyl-1-(4-nitrophenyl)-1H-imidazoleYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (4.87 g, 122.0 mmol, 60% dispersion in oil) was added to a solution of 2-methylimidazole (10 g, 122.0 mmol) in DMF (100 ml) and stirred at room temperature for 0.25 h. 1-Fluoro-4-nitrobenzene (17.18 g, 122.0 mmol) was added to the reaction mixture and stirred at room temperature for 16 h. Water (150 ml) and ethyl acetate (250 ml) were added, the aqueous separated and extracted with ethyl acetate (3×150 ml). The combined extracts were washed with water (3×150 ml), dried (Na2SO4) and evaporated to give the desired product (11.5 g, 47%); δ (360 MHz, CDCl3) 2.24 (3H, s, Me); 7.06 (1H, d, J=1.5 Hz, Ar-H); 7.10 (1H, d, J=1.5 Hz, Ar-H); 7.50 (2H, d, J=9.5 Hz, Ar-H); 8.38 (2H, d, J=9.5 Hz, Ar-H).

Workup

  1. stirringstirred at room temperature for 16 h
  2. customthe aqueous separated
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe combined extracts were washed with water (3×150 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0cfac66b5d5142f4b7b7e486ebe6d296
Source dataset
uspto-grants-1994_03
Patent number
US05298520

Reaction notes

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