Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](Cl)(=[O:12])=[O:11])=[O:4].[NH2:14][C:15]1[O:19][N:18]=[C:17]([CH3:20])[C:16]=1[CH3:21]>N1C=CC=CC=1>[CH3:20][C:17]1[C:16]([CH3:21])=[C:15]([NH:14][S:10]([C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:11])[O:19][N:18]=1Komponenten
Versuchsvorschrift
2-Methoxycarbonylthiophene-3-sulfonyl chloride (2.50 g, 10.05 mmol) was added to a solution of 5-amino-3,4-dimethylisoxazole(0.98 g, 8.75 mmol) in dry pyridine (5.0 ml). The reaction mixture was stirred at room temperature for 16 h. Pyridine was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was washed with 1N HCl (2×50 ml) and dried over anhydrous magnesium sulfate. Evaporation of the solvents left an oily residue, which, after purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent), yielded 2.20 mg (65%) of a brown solid. Further purification was achieved by recrystallization from ethyl acetate/hexanes, giving the pure product as a white solid, m.p. 113°-116° C.
Aufarbeitung
- customPyridine was removed under reduced pressure
- customthe residue was partitioned between water and dichloromethane
- washThe organic layer was washed with 1N HCl (2×50 ml)
- dry with materialdried over anhydrous magnesium sulfate
- customEvaporation of the solvents
- waitleft an oily residue, which
- customafter purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent)
Quellen und Nachweise
- ORD-Eintrag
- ord-a980ca657da34400a5d38a3146522957
- Quelldatensatz
- uspto-grants-1997_01
- Patentnummer
- US05594021
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