Reaktionsgleichung
F[C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[CH3:22])[C:12]2=[O:23])=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].[H-].[Na+].CO.C(Cl)Cl>CN(C=O)C.C(Cl)(Cl)Cl>[O:6]1[C:2]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:15][CH2:14][N:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:21]=4[CH3:22])[C:12]3=[O:23])=[CH:7][C:3]=2[CH:4]=[N:5]1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime (I-113b:160 mg, 0.509 mmol) in dry DMF (2 mL) was added dropwise to a stirred mixture of NaH (72 mg, 1.52 mmol) in DMF (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 70 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The aqueous layer was distilled to afford the solid residue which was dissolved 1:1 DCM:MeOH. The crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3). The residue was washed with hexane and dried to afford 105 mg of the product (70.4% yield).
Aufarbeitung
- customThe reaction mixture was partitioned between ice water and ethylacetate
- distillationThe aqueous layer was distilled
- customto afford the solid residue which
- customThe crude product was purified by column chromatography on silica gel (4-5% MeOH in CHCl3)
- washThe residue was washed with hexane
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-a43f94ed67a64d45848ca14060d1cedc
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- USRE045173E1
Verknüpfte Notizen
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