Sodium Hydroxide → 1-(4-Bromo-2-methoxyphenyl)-4-methyl-1H-imidazole

HRID 2247479Notes

Reaction equation

HRID 2247479 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13](=O)[CH3:14])[C:9](=O)C)=[C:4]([O:16][CH3:17])[CH:3]=1.C([O-])(=O)C.[NH4+:22].[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:13]([CH3:14])[N:22]=[CH:9]2)=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 66960203HCID 66960203, compound

Product 1

HCID 534156611-(4-Bromo-2-methoxyphenyl)-4-methyl-1H-imidazoleYield 93.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(4-bromo-2-methoxyphenyl)-N-(2-oxopropyl)acetamide (23.4 g), ammonium acetate (31.5 g), and acetic acid (49 g) was agitated under heating at 120° C. for 30 minutes. After the reaction solution was neutralized with sodium hydroxide under ice-cooling, the reaction solution was extracted with ethyl acetate. 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: hexane-ethyl acetate system), and 19.4 g of the title compound was obtained.

Workup

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

Sources & evidence

ORD record
ord-13c1949fe24d4eb08857346d321e6379
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

Loading…