Imidazole → HCID 86602468, compound

HRID 1446461Notes

Reaction equation

HRID 1446461 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH:10]=[O:11].O.N>[Cu].C(OCC)(=O)C>[N:1]1([C:12]2[CH:13]=[C:14]([O:15][CH3:16])[CH:7]=[CH:8][C:9]=2[CH:10]=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 986623-Bromo-4-methoxybenzaldehydeHCID 12896473Azane;hydrate

Product 1

HCID 86602468HCID 86602468, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To an aqueous solution (15 mL) of imidazole (5.69 g), 3-bromo-4-methoxybenzaldehyde (3.00 g) and copper powder (86 mg) were added, and the reaction solution was agitated for three days at 100° C. under nitrogen atmosphere. A concentrated ammonia water and ethyl acetate were added to the reaction mixture, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:ethyl acetate), and 321 mg of the title compound was obtained.

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with a saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent:ethyl acetate)

Sources & evidence

ORD record
ord-0ad2d67193c24aef9ad2241c30a35aea
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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