Imidazole → 1-(2,5-Dimethoxy-3,4,6-trimethylbenzyl)imidazole

HRID 484029Notes

Reaction equation

HRID 484029 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:6][O:7][C:8]1[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([O:18][CH3:19])=[C:12]([CH3:20])[C:9]=1[CH2:10]Br>CN(C)C=O.C(N(CC)CC)C.O>[CH3:19][O:18][C:13]1[C:14]([CH3:17])=[C:15]([CH3:16])[C:8]([O:7][CH3:6])=[C:9]([CH3:10])[C:12]=1[CH2:20][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 2

HCID 795ImidazoleHCID 142777601-(Bromomethyl)-2,5-dimethoxy-3,4,6-trimethylbenzene

Product 1

HCID 142777611-(2,5-Dimethoxy-3,4,6-trimethylbenzyl)imidazoleYield 47.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 499 mg (7.33 mmol) of imidazole and 2.0 g (7.33 mmol) of 2,5-dimethoxy-3,4,6-trimethylbenzyl bromide in 12 ml of dimethylformamide, 1.2 ml of triethylamine was added and stirred at room temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried, from which the solvent was evaporated off. The residue was purified with silica gel column chromatography (chloroform-methanol(1:1)) and recrystallized from isopropyl ether, to give 0.9 g (47.3%) of 1-(2,5-dimethoxy-3,4,6-trimethylbenzyl)imidazole. m.p. 82°-83° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried, from which the solvent
  4. customwas evaporated off
  5. customThe residue was purified with silica gel column chromatography (chloroform-methanol(1:1))
  6. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-93ac8646a3404b3da250f8538187c352
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

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