1-(2,4-Dichlorophenyl)-2-phenylpropen-1-one → 3-[1-[3-(2,4-Dichlorophenyl)-3-oxo-2-phenylpropyl]imidazol-4-yl]propanoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

3-(Imidazol-4-yl)propanoic acid methyl ester (4 g) was added to a solution of 1-(2,4-dichlorophenyl)-2- phenylpropen-1one (7.5 g) in ethanol (50 ml) and the resulting solution maintained at 20° C. for 12 hours. The solvent was removed under reduced pressure to yield 3-[1-[3-(2,4-dichlorophenyl)-3-oxo-2-phenylpropyl]imidazol-4-yl]propanoic acid methyl ester (12 g) as an oil. A portion of the oil (3 g) was dissolved in dimethylformamide (50 ml) and copper-II-chloride dihydrate (10 g) added to the solution. The resulting solution was heated at 80° C. for 18 hours and then cooled to room temperature. Water was added to the reaction mixture and the aqueous phase extracted twice with ethyl acetate. The organic phases were combined, washed with dilute aqueous ammonia, water, and brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield a gum (2.75 g). The gum was chromatographed on silica gel eluting with a mixture of methanol:dichloromethane (1.5:98.5) to yield an oil upon treatment with ethereal hydrogen chloride yielded the hydrochloride salt of 3-[ 1-[2-chloro-3-(2,4-dichlorophenyl)-3-oxo-2-phenylpropyl]imidazol-4-yl]propanoic acid methyl ester (1.56 g), m.p. 144-7° C., (Found: C, 52.75; H, 4.13; N, 5.57%; C22H20Cl4N2O3 requires C, 52.61; H, 4.01; N, 5.58%), having the formula: ##STR31##

Provenance & Evidence