Reaktionsgleichung
[CH3:1][C:2]1[O:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:26]([C:28]1[CH:42]=[CH:41][C:31]([S:32][C:33]2[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1)[CH3:27]>ClCCl>[CH2:26]([C:28]1[CH:42]=[CH:41][C:31]([S:32][C:33]2[CH:40]=[CH:39][C:36]([CH2:37][NH:38][C:8]([C:4]3[O:3][C:2]([CH3:1])=[N:6][C:5]=3[CH3:7])=[O:10])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1)[CH3:27]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred mixture of 2,4-dimethyl-1,3-oxazole-5-carboxylic acid (155 mg, 1.1 mM) and dichloromethane (20 ml) was added 1,3-dicyclohexylcarbodiimide (227 mg, 1.1 mM) at 0°-10° C., and the mixture was stirred for 30 min at the same temperature. To this was added dropwise a solution (10 ml) of 4-(4-ethylthiophenoxy)benzylamine (285 mg, 1.1 mM) in dichloromethane, and the mixture was stirred for 12 h at room temperature. The mixture was poured into ice water, and the mixture was extracted with dichloromethane. The extract was washed with saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-[4-(4-ethylthiophenoxy)benzyl]-2,4-dimethyl-1,3-oxazole-5-carboxamide (164 mg, 39%) as colorless crystals, m.p. 60.0°-64.5° C.
Aufarbeitung
- stirringthe mixture was stirred for 12 h at room temperature
- extractionthe mixture was extracted with dichloromethane
- washThe extract was washed with saturated ammonium chloride solution and brine
- dry with materialdried with magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was chromatographed over silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-9bf5f7adc5fd40939760c7953f06fb16
- Quelldatensatz
- uspto-grants-1993_11
- Patentnummer
- US05264448
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