Chloroacetaldehyde → 2-(3-methoxyphenyl)-1-phenyl-1H-imidazole

HRID 539483

Reaction equation

HRID 539483 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6](=[NH:14])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:19][CH:20]=O.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:19]=[CH:20][N:14]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 178490388HCID 178490388, compound

Product 1

HCID 571284632-(3-methoxyphenyl)-1-phenyl-1H-imidazoleYield 75.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a 500 mL round bottom flask was added 3-methoxy-N-phenylbenzimidamide (7.81 g, 34.5 mmol), 2-chloroacetaldehyde solution (50%, 9.4 mL, 69 mmol), sodium bicarbonate (5.80 g, 69 mmol), and 150 mL 2-propanol. The reaction mixture was heated at reflux for 3 h under nitrogen. The solvent was removed under vacuum and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed with water, brine, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography eluting with 50% and 100% ethyl acetate/hexane to give pure product (6.52 g, 75%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h under nitrogen
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography
  10. washeluting with 50% and 100% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9dbcc9fbbfd64b0e8b40a96957ed0d9f
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Linked notes

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