Imidazole → HCID 21287220, compound

HRID 868533Notes

Reaction equation

HRID 868533 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH:7]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].O>CN(C)C=O>[N:1]1([CH:7]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 21287219HCID 21287219, compound

Product 1

HCID 21287220HCID 21287220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Imidazole (10.21 g, 150 mmole) was dissolved in dimethylformamide (20 ml) and ω-bromo-2-(2,4-dichlorobenzyloxy)acetophenone (11.2 g, 29.9 mmole) was added slowly. After stirring for 2.5 hours with ice-cooling, water (120 ml) was added and the mixture was extracted with ethyl acetate (120 ml×2). The extract was washed with water (120 ml×2) and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to chromatography on a silica gel columne and eluted with methanol/chloroform to obtain the title compound (8.37 g, 77.2%), m.p. 109°-111° C. (recrystallized from n-hexane/benzene).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (120 ml×2)
  3. washThe extract was washed with water (120 ml×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure
  6. washeluted with methanol/chloroform
  7. customto obtain
  8. customthe title compound (8.37 g, 77.2%), m.p. 109°-111° C. (recrystallized from n-hexane/benzene)

Sources & evidence

ORD record
ord-7fdbb7bf8904473c93d090785a66f0d5
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

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