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

HRID 2069281Notes

Reaction equation

HRID 2069281 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][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[CH:30][NH:31][CH:32]=2)=[CH:24][CH:23]=1.C(OCC)(=O)C.O>O1CCCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:31]2[CH:32]=[C:28]([C:25]3[CH:24]=[CH:23][C:22]([CH2:21][O:20][CH3:19])=[CH:27][CH:26]=3)[N:29]=[CH:30]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 178494485HCID 178494485, compound

Product 1

HCID 589645075-[4-(4-Methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl esterYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.00 g (3.74 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester and 0.775 g (4.12 mmol) of 4-(4-methoxymethyl-phenyl)-1H-imidazole in 10 ml of tetrahydrofuran are refluxed for 2 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 (40-63 μm particle size) with ethyl acetate/hexane 2:3, yielding 1.55 g of 5-[4-(4-methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester acid as a yellow powder, m.p.=135-137° C. 1H-NMR (DMSO-d6, 400 MHz): 3.30 s, 3H; 3.95 s, 3H; 4.42 s, 3H; 7.35 d, J 10.4 Hz, 2H; 7.82 d, J=10.4 Hz, 2H; 8.02 s, 1H; 8.05 s, 1H; 8.30 s, 1H; 8.72 s, 1H.

Workup

  1. temperatureare refluxed for 2 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 (40-63 μm particle size) with ethyl acetate/hexane 2:3

Sources & evidence

ORD record
ord-af7ff16dce3640308b088a6ca7132174
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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