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

HRID 1075451Notes

Reaction equation

HRID 1075451 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>[Cu].O>[N:11]1([C:2]2[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

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

Product 1

HCID 8179761-(3-nitrophenyl)-1H-imidazoleYield 79.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent2×

Conditions

Temperature
200 °C

Procedure

A mixture of 1 -iodo-3-nitrobenzene (90g, 0.36mol), imidazole (54g, 0.79mol), potassium carbonate (54g, 0.39mol) and finely divided copper powder (1 g) is heated to 200° C. The melt is stirred for 2 hours under nitrogen. During the reaction water vapor is trapped by molecular sieves, placed between the reaction vessel and the condenser. Following the reaction the mixture is cooled to 100° C. and water is added. The mixture is allowed to cool to room temperature and the crude product is filtered off and dried. Recrystallization from toluene (200-250ml) affords pure 3-(1-imidazolyl)nitrobenzene (54.2g, 79%). Mp 101-102° C.

Workup

  1. customthe reaction the mixture
  2. temperatureis cooled to 100° C.
  3. temperatureto cool to room temperature
  4. filtrationthe crude product is filtered off
  5. customdried
  6. customRecrystallization from toluene (200-250ml)

Sources & evidence

ORD record
ord-bde6a04547a7462f8f05be75cc14764f
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

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