Methane → 1-(3-nitrophenyl)-1H-imidazole

HRID 2086073Notes

Reaction equation

HRID 2086073 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.C>C1(C)C=CC=CC=1.[Cu].O>[N+:8]([C:4]1[CH:3]=[C:2]([N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

8

Reactant 4

HCID 297MethaneHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 125741-Iodo-3-nitrobenzene

Product 1

HCID 8179761-(3-nitrophenyl)-1H-imidazoleYield 71.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

An intimate mixture of 1-iodo-3-nitrobenzene (24.9 g, 0.1 mol), copper bronze (320 mg, 5 mmol), potassium carbonate (15.2 g, 0.11 mol) and imidazole (15.0 g, 0.22 mol) was heated under a stream of nitrogen at 200° C. for 90 minutes. The reaction was cooled to 100° C., carefully treated with water (750 ml) and the resulting suspension stirred to ambient temperature over 16 hours. Filtration gave a grey-coloured solid which was dissolved in hot toluene (125 ml) and treated with decolourising charcoal (2 g). Filtration and cooling afforded 1-(3-nitrophenyl)-1H-imidazole as pale green needles (13.5 g, 71%). δH (360 MHz, CDCl3) 7.29 (1H, br s), 7.38 (1H, br s), 7.68-7.78 (2H, m), 7.97 (1H, br s), 8.23-8.29 (2H, m).

Workup

  1. temperatureThe reaction was cooled to 100° C.
  2. filtrationFiltration
  3. customgave a grey-coloured solid which
  4. filtrationFiltration
  5. temperaturecooling

Sources & evidence

ORD record
ord-e8dda8b177c24e49b88b46f170da82b5
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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