Water → 5-[4-(4-Methoxy-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069278Notes

Reaction equation

HRID 2069278 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[CH:29][NH:30][CH:31]=2)=[CH:23][CH:22]=1.C(OCC)(=O)C.O>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:30]2[CH:31]=[C:27]([C:24]3[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=3)[N:28]=[CH:29]2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl esterHCID 178418716HCID 178418716, compound

Product 1

HCID 589645045-[4-(4-Methoxy-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl esterYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.200 g (4.49 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester and 0.861 g (4.94 mmol) of 4-(4-methoxy-phenyl)-1H-imidazole in 15 ml of tetrahydrofuran are refluxed for 5 hours. After cooling, the reaction mixture is distributed between ethyl acetate and water, the organic phase separated and washed with brine, dried over Na2SO4 and concentrated to dryness. The residue is purified by flash chromatography on silica (20 μm particle size) with ethyl acetate/hexane 2:3, yielding 1.511 g of 5-[4-(4-methoxy-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester as a yellow powder. 1H-NMR (DMSO-d6, 400 MHz): 3.80 s, 3H; 3.95 s, 3H; 7.00 d, J=10.4 Hz, 2H; 7.78 d, J=10.4 Hz, 2H; 7.95 s, 1H; 8.00 s, 1H; 8.28 s, 1H; 8.72 s, 1H.

Workup

  1. temperatureare refluxed for 5 hours
  2. temperatureAfter cooling
  3. customthe organic phase separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by flash chromatography on silica (20 μm particle size) with ethyl acetate/hexane 2:3

Sources & evidence

ORD record
ord-5578fd2c740647859322dfe417ae2414
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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