Imidazole → HCID 13749943, compound

HRID 1248993Notes

Reaction equation

HRID 1248993 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[CH2:11].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH:10]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH2:11][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 544030331-(2,4-Dichlorophenyl)-2-(4-methylphenyl)propen-1-one

Product 1

HCID 13749943HCID 13749943, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2,4-dichlorophenyl)-2-(4-methylphenyl)propen-1-one (660 mg) and imidazole (770 mg) in ethanol (10 ml) were stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield a gum. The gum was chromatographed on silica gel in methanol: dichloromethane (1:24) to yield 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-(4-methylphenyl)propan-1-one (450 mg) (Found: C, 78.25; H, 5.88; N, 9.53; C19H18N2O requires C, 78.62; H, 6.21; N, 9.66) which was treated with ethereal hydrogen chloride to yield the hydrochloride salt of 1-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-2-(4-methylphenyl)propan-1-one m.p. 92°-96° C. (Found: C, 54.79; H, 4.33; N, 6.59; C19H17Cl3N2O.H2O requires C, 55.16; H, 4.38; N, 6.77) having the formula: ##STR25##

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto yield a gum
  7. customThe gum was chromatographed on silica gel in methanol: dichloromethane (1:24)

Sources & evidence

ORD record
ord-cbe4c9f87216417287199d3376301e94
Source dataset
uspto-grants-1986_12
Patent number
US04628104

Reaction notes

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