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

HRID 393366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393366
Cl[C:2]1[N:7]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])[C:11]([Cl:24])=[CH:10][C:9]=2[F:25])[C:6](=[O:26])[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[N:3]=1.[C:31]1(=[N:36][OH:37])[CH2:35][CH2:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>O>[Cl:24][C:11]1[C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])=[CH:13][C:8]([N:7]2[C:6](=[O:26])[CH:5]=[C:4]([C:27]([F:30])([F:29])[F:28])[N:3]=[C:2]2[O:37][N:36]=[C:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:9]([F:25])[CH:10]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 14500Cyclopentanone, oximeHCID 102386332-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone

Produkt 1

HCID 226602383-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-2-[(1-cyclopentylidene)aminooxy]-6-trifluoromethyl-4(3H)-pyrimidinoneAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-3-[4-chloro-2-fluoro-5-(2-nitrophenoxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone(1.28 g, 0.0027 mol), cyclopentanone oxime(027 g, 0.0027 mol), potassium carbonate(0.38 g, 0.027 mol) and tetrahydrofuran(11 ml) was heated under reflux for 3 hours. The reaction mixture was poured into water, extracted with ethyl acetate, and washed with brine. The organic phase was dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel(20% ethyl acetate/hexane) to give compound II-3 (1.23 g, yield 84.7%) as a white amorphous solid, m.p.76-78° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel(20% ethyl acetate/hexane)
  8. customto give compound II-3 (1.23 g, yield 84.7%) as a white amorphous solid, m.p.76-78° C.

Quellen und Nachweise

ORD-Eintrag
ord-bd04dc98f49b41f38d2df63e165da3de
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806367B2

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