Chloroacetaldehyde → 1-(2,6-diisopropylphenyl)-2-(3-methoxy-5-methylphenyl)-1H-imidazole

HRID 539454Notes

Reaction equation

HRID 539454 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[NH:24])[C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([O:22][CH3:23])[CH:16]=1)([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl[CH2:31][CH:32]=O.CC(O)C>O.C(OCC)(=O)C>[CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[N:13]1[CH:32]=[CH:31][N:24]=[C:14]1[C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([O:22][CH3:23])[CH:16]=1)([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 33ChloroacetaldehydeHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 178490167HCID 178490167, compound

Product 1

HCID 706543401-(2,6-diisopropylphenyl)-2-(3-methoxy-5-methylphenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round bottom flask was mixed N-(2,6-diisopropylphenyl)-3-methoxy-5-methylbenzimidamide (5.83 g, 17.97 mmol), sodium bicarbonate (3.02 g, 35.9 mmol), 2-chloroacetaldehyde (50%, 4.56 ml, 35.9 mmol), and 80 mL of 2-propanol. The reaction mixture was heated to reflux for 3 hours under nitrogen. The reaction mixture was diluted with water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with 10% LiCl solution, brine, dried over magnesium sulfate, filtered, evaporated leaving a brown oil. The oil was purified by column chromatography eluting with 20% ethyl acetate/hexane (5.78 g, 92%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours under nitrogen
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe organic layers were washed with 10% LiCl solution, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customleaving a brown oil
  10. customThe oil was purified by column chromatography
  11. washeluting with 20% ethyl acetate/hexane (5.78 g, 92%)

Sources & evidence

ORD record
ord-f27f4972964c47fc88f266fa7d8c3270
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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