Potassium Carbonate → 4-Methyl-1-(2-(trifluoromethyl)-4-nitrophenyl)-1H-imidazole

HRID 535843Notes

Reaction equation

HRID 535843 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[C:17]([F:18])([F:19])[F:20])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 178418800HCID 178418800, compound

Product 1

HCID 587242874-Methyl-1-(2-(trifluoromethyl)-4-nitrophenyl)-1H-imidazoleYield 81.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-methylimidazole (0.63 g, 7.67 mmol), 1-fluoro-2-(trifluoromethyl)-4-nitrobenzene (1.06 g, 5.1 mmol), and K2CO3 (1.06 g, 7.67 mmol) in acetonitrile (20 mL) was refluxed for 6 hs. The mixture was filtered through Celite and filtrate was evaporated in vacuo and the residue was purified by chromatography on silica gel (PE/EtOAc 1:1) to give 1.13 g product as light green oil (81.8%). 1H NMR (300 MHz, CDCl3) δ: 8.71 (1H, s), 8.52-8.55 (1H, d, J=8.4 Hz), 7.59-7.62 (2H, m), 6.90 (1H, s), 2.32 (3H, s). LCMS: m/z [M+H]+ 272.0660.

Workup

  1. temperaturewas refluxed for 6 hs
  2. filtrationThe mixture was filtered through Celite and filtrate
  3. customwas evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel (PE/EtOAc 1:1)

Sources & evidence

ORD record
ord-89347dd545204dd3846659a395f8edcb
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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