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

HRID 34488Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:29])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH2:22]>C(O)C>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][C:6]1[N:7]=[CH:8][N:9]([CH2:22][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])=[O:29])[CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

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##

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-b52d0b8db94f4bb5be336e7934f6b0f2
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04761483

Reaction notes

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