Water → 3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-2-[(1-ethoxyethylidene)aminooxy]-6-trifluoromethyl-4(3H)-pyrimidinone

HRID 393365

Reaktionsgleichung

[OH:1][N:2]=[C:3]([O:5][CH2:6][CH3:7])[CH3:4].[H-].[Na+].Cl[C:11]1[N:16]([C:17]2[CH:22]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N+:30]([O-:32])=[O:31])[C:20]([Cl:33])=[CH:19][C:18]=2[F:34])[C:15](=[O:35])[CH:14]=[C:13]([C:36]([F:39])([F:38])[F:37])[N:12]=1.O>O1CCCC1>[Cl:33][C:20]1[C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N+:30]([O-:32])=[O:31])=[CH:22][C:17]([N:16]2[C:15](=[O:35])[CH:14]=[C:13]([C:36]([F:38])([F:39])[F:37])[N:12]=[C:11]2[O:1][N:2]=[C:3]([O:5][CH2:6][CH3:7])[CH3:4])=[C:18]([F:34])[CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Ethyl N-hydroxyacetimidate(0.23 g, 0.002 mol) was added dropwise to a suspension of sodium hydride(008 g, 0.002 mol) in tetrahydrofuran(5 ml) with stirring at 0° C. 2-Chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone(0.93 g, 0.002 mol) was added to the mixture at 0° C., and the mixture was stirred at 0° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate solution was concentrated and purified by column chromatography on silica gel(20% ethyl acetate/hexane) to give compound II-1 (0.90 g, yield 85%) as a white solid, m.p.152-155° C.

Aufarbeitung

stirringthe mixture was stirred at 0° C. for 3 hours
extractionextracted with ethyl acetate
concentrationThe ethyl acetate solution was concentrated
custompurified by column chromatography on silica gel(20% ethyl acetate/hexane)
customto give compound II-1 (0.90 g, yield 85%) as a white solid, m.p.152-155° C.

Quellen und Nachweise

ORD-Eintrag: ord-0462b6f913884dfabc6c95d62f226078
Quelldatensatz: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06806367B2

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