Imidazole → 1-(2,4-Dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one

HRID 34487Notes

Reaction equation

HRID 34487 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:11][N:19]1[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 1294381-(2,4-Dichlorophenyl)-2-phenylpropen-1-one

Product 1

HCID 137499421-(2,4-Dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2,4-dichlorophenyl)-2-phenylpropen-1-one (4g), imidazol (1.36 g) and tetramethylquanidine (0.5 ml) in tetrahydrofuran (100 ml) was heated at reflux for 12 hours. The reaction mixture was cooled and concentrated under reduced pressure to yield a gum. The gum was dissolved in ethyl acetate, washed with distilled water, and acidified with 4N hydrochloric acid. The aqueous phase was basified with sodium carbonate and extracted with ethyl acetate. The organic phase was separated, washed with distilled water, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield an oil which was chromatographed on silica gel using a mixture of methanol/dichloromethane (1:9) as an eluent to yield 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one (600 mg), which was treated with ethereal hydrogen chloride to yield the hydrochloride salt of 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-phenylpropan-1-one, m.p. 110° C., (Found: C, 55.38; H, 4.37; N, 7.40%; C18H15Cl3N2O.1/2H2O requires C, 55.34; H, 4.13; N, 7.17%) having the formula: ##STR28##

Workup

  1. temperatureat reflux for 12 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customto yield a gum
  5. washwashed with distilled water
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was separated
  8. washwashed with distilled water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customto yield an oil which
  12. customwas chromatographed on silica gel using
  13. additiona mixture of methanol/dichloromethane (1:9) as an eluent

Sources & evidence

ORD record
ord-991c45a866e3470fb33e38814f1b128a
Source dataset
uspto-grants-1988_08
Patent number
US04761483

Reaction notes

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