Imidazole → 2-(4-NITRO-BENZYL)-1H-IMIDAZOLE

HRID 1249543Notes

Reaction equation

HRID 1249543 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 104428612-(4-NITRO-BENZYL)-1H-IMIDAZOLEYield 68.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 13.6 g of imidazole, 43.2 g of p-bromomethylnitrobenzene and 55.2 g of anhydrous potassium carbonate in 300 ml of dry toluene was refluxed for 18 hours. After concentration under reduced pressure, 200 ml of dichloromethane was added to the residue and insoluble salts were filtered off. The filtrate was evaporated and the residue was chromatographed on silica gel using dichloromethane-ethanol (20:1 by volume) to give 27.9 g of p-(1-imidazolylmethyl)nitrobenzene as pale yellow platelets. Then, a solution of 2.0 g of this product in 50 ml of ethanol was hydrogenated over 0.2 g of palladium on carbon at room temperature under a hydrogen pressure of 4 atms. After filtration and evaporation, the residual solid was recrystallized from ethanol-diethyl ether-petroleum ether to give 1.4 g of p-(1-imidazolylmethyl)aniline as colorless needles. M.P.: 134°-137° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationAfter concentration under reduced pressure, 200 ml of dichloromethane
  3. additionwas added to the residue and insoluble salts
  4. filtrationwere filtered off
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-754e0c970e384823a0383e354d45977a
Source dataset
uspto-grants-1986_12
Patent number
US04632934

Reaction notes

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