Imidazole → 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone

HRID 1582614Notes

Reaction equation

HRID 1582614 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17])=[O:9]>CN(C)C=O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([OH:17])=[C:10]([C:8](=[O:9])[CH2:7][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:15]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27568852-Bromo-5'-chloro-2'-hydroxyacetophenone2×

Product 1

HCID 129536551-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanoneYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (17.9 g, 0.26 mol) was added to a solution of 2-bromo-1-(5-chloro-2-hydroxyphenyl)-1-ethanone [compound (4-1)] (21.8 g, 87.7 mmol) in N,N-dimethylformamide (50 mL), and the resultant mixture was stirred for 17 hours at room temperature. The reaction mixture was added to ice-water, followed by extraction with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate. Subsequently, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography, followed by drying under reduced pressure, to thereby yield 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone as colorless crystals (17.1 g, yield: 82.4%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customSubsequently, the solvent was removed under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. customby drying under reduced pressure

Sources & evidence

ORD record
ord-a2e803ce38484b88960817480b1e54ba
Source dataset
uspto-grants-2004_05
Patent number
US06737434B2

Reaction notes

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