2-Methylimidazole → 1-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazole

HRID 2075979Notes

Reaction equation

HRID 2075979 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.C[C:13]1[NH:14][CH:15]=[CH:16][N:17]=1.[CH:18](N(CC)C(C)C)(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:17]1[CH:16]=[C:15]([CH3:18])[N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 218765961-(2-fluoro-4-nitrophenyl)-4-methyl-1H-imidazoleYield 42.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Difluoronitrobenzene (7.97 g, 50 mmol), 2-methylimidazole (4.51 g, 55 mmol) and N,N-diisopropylethylamine (16.16 g, 125 mmol) were dissolved in acetonitrile (80 mL) and the reaction was heated to reflux for 24 hours under an atmosphere of nitrogen. The solvent was evaporated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and heptane to yield the title compound (4.66 g, 42%) as a pale-yellow solid. MS ISP (m/e): 222.1 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=8.42 (d, 1H), 8.21 (d, 1H), 8.11 (s, 1H), 7.95 (t, 1H), 7.43 (s, 1H), 2.19 (s, 3H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 24 hours under an atmosphere of nitrogen
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was crystallized from a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-70fbe9d2d1d14233b4a0904501efbe7b
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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