Dimethyl Sulfoxide → Methyl 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-oxazolepropionate

HRID 47929

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of methyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (805.4 g), 2-methylimidazole (1101.7 g) and dimethyl sulfoxide (2416 mL) was stirred at 110° C. for 8 h and water was added to the obtained mixture. The mixture was extracted with ethyl acetate and the extract was washed with 5% brine. The solvent was evaporated and the residue was dissolved in ethyl acetate (1611 mL) with heating. n-Heptane (4832 mL) was added at 30° C. The precipitated crystals were collected by filtration and washed with ethyl acetate-n-heptane (1:3) to give the title compound (716.6 g, yield: 77.2%).

Aufarbeitung

extractionThe mixture was extracted with ethyl acetate
washthe extract was washed with 5% brine
customThe solvent was evaporated
dissolutionthe residue was dissolved in ethyl acetate (1611 mL)
temperaturewith heating
additionn-Heptane (4832 mL) was added at 30° C
filtrationThe precipitated crystals were collected by filtration
washwashed with ethyl acetate-n-heptane (1:3)

Quellen und Nachweise

ORD-Eintrag: ord-17cef38e09974a86a973c413bdd31925
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06699995B1

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