Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1.C([O-])(=O)C.[NH4+:36]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:36][C:28]([C:27]3[CH:30]=[CH:31][C:24]([N:21]4[CH2:22][CH2:23][O:18][CH2:19][CH2:20]4)=[CH:25][CH:26]=3)=[N:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1Komponenten
Versuchsvorschrift
Ethyl 3-(4-chlorophenyl)-2-hydroxyimino-3-oxopropionate (200 g), 4-morpholinobenzaldehyde (244.4 g) and ammonium acetate (603 g) were refluxed under heating for 15 hr in acetic acid, and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform (2 L), and the solution was neutralized with a saturated aqueous hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after drying, the solvent was evaporated under reduced pressure and crude crystals were obtained from ethyl acetate. The crude crystals were subjected to silica gel column chromatography to give the objective ethyl 5-(4-chlorophenyl)-2-(4-morpholinophenyl)imidazole-4-carboxylate (78 g), melting point 215° C.
Aufarbeitung
- customthe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in chloroform (2 L)
- extractionextracted with chloroform
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customafter drying
- customthe solvent was evaporated under reduced pressure
- customcrude crystals were obtained from ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-3ff0c9e84cce40eca2cca31ea61478fd
- Quelldatensatz
- uspto-grants-2001_09
- Patentnummer
- US06288061B1
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