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

HRID 539463Notes

Reaction equation

HRID 539463 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:5](=[NH:19])[NH:6][C:7]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17].Cl[CH2:25][CH:26]=O.C(=O)(O)[O-].[Na+].CC(O)C>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:6]([C:7]3[C:8]([CH:16]([CH3:17])[CH3:18])=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]([CH3:15])[CH3:14])[CH:25]=[CH:26][N:19]=2)[CH:20]=[C:21]([CH3:23])[CH:22]=1

Participants

7

Reactant 4

HCID 33ChloroacetaldehydeHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 178422447HCID 178422447, compound

Product 1

HCID 706547082-(3-bromo-5-methylphenyl)-1-(2,6-diisopropylphenyl)-1H-imidazoleYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round bottom flask was added 3-bromo-N-(2,6-diisopropylphenyl)-5-methylbenzimidamide (2.92 g, 7.82 mmol), 2-chloroacetaldehyde (50%, 2.456 g, 15.64 mmol), sodium bicarbonate (1.314 g, 15.64 mmol), 60 mL 2-propanol. The reaction mixture was heated to reflux overnight under nitrogen. The reaction mixture was cooled and diluted with ethyl acetate and water. 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, and evaporated. The material was purified by column chromatography eluting with 15 and 20% ethyl acetate/hexane to give desired product (2.45 g, 79%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight under nitrogen
  3. temperatureThe reaction mixture was cooled
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe organic layers were washed with 10% LiCl solution, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe material was purified by column chromatography
  11. washeluting with 15 and 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0d77aeb3e3864008916de191f5f86c6c
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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