Dimethylformamide → 5-methyl-1-(4-nitrobenzyl)-1H-imidazole

HRID 30694

Reaction equation

HRID 30694 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1)([O-:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:1][C:2]1[N:3]([CH2:14][C:13]2[CH:16]=[CH:17][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=2)[CH:4]=[N:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 178418800HCID 178418800, compound

Product 1

HCID 4266335-methyl-1-(4-nitrobenzyl)-1H-imidazoleYield 3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-methyl-1H-imidazole (25.5 g), 4-nitrobenzyl bromide (56 g), potassium carbonate (86 g) and N,N-dimethylformamide (500 ml) was stirred at room temperature for 14 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 5-methyl-1-(4-nitrobenzyl)-1H-imidazole (1.6 g, 3%) as crystals from a fraction eluted with methanol-ethyl acetate (1:20, v/v). Recrystallization thereof from ethyl acetate-isopropyl ether gave colorless prism crystals. melting point: 120-121° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b7b3efceb2e420bba2ba80e31ff815e
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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