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

HRID 539487Notes

Reaction equation

HRID 539487 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)/[C:5](=[N:7]\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[NH2:6].Cl[CH2:18][CH:19]=O.C(=O)(O)[O-].[Na+].CC(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:18]=[CH:19][N:6]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 178511971HCID 178511971, compound

Product 1

HCID 706543692-(3-bromophenyl)-1-phenyl-1H-imidazoleYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-3-bromo-N′-phenylbenzimidamide (6.95 g, 25.3 mmol), 2-chloroacetaldehyde (6.94 g, 44.2 mmol) and sodium bicarbonate (5.30 g, 63.1 mmol) were charged into the reaction flask with 200 mL of 2-propanol. This reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature, was diluted with 200 mL of water then was extracted with ethyl acetate. The extracts were washed with aqueous lithium chloride then were dried over magnesium sulfate. These dried extracts were then filtered and stripped under vacuum. The crude residue was passed through a silica gel column using 30-35% ethyl acetate/hexanes yielding 2-(3-bromophenyl)-1-phenyl-1H-imidazole (2.8 g, 9.36 mmol, 37% yield).

Workup

  1. temperatureThis reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionthen was extracted with ethyl acetate
  4. washThe extracts were washed with aqueous lithium chloride
  5. dry with materialthen were dried over magnesium sulfate
  6. filtrationThese dried extracts were then filtered

Sources & evidence

ORD record
ord-d151637ca99746dfbe0b2e50a76ca989
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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