Dabco → Azoxystrobin

HRID 1645235

Reaktionsgleichung

Reaktionsgleichung von HRID 1645235
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[OH:31])#[N:24].C(=O)([O-])[O-].[K+].[K+].C1N2CCN(CC2)C1>O.CC(CC(C)=O)C>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1)#[N:24]

Komponenten

7

Edukt 4

HCID 9237DabcoHCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Produkt 1

HCID 3034285AzoxystrobinAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 7909Methyl Isobutyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
47.5 °C

Versuchsvorschrift

Methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (98.4 g at 97.7% strength; prepared as described in WO 92/08703) was added to MIBK (210 g) and water (38.3 g) and heated to 45-50° C. 2-Cyanophenol (40.1 g), potassium carbonate (63.4 g) and DABCO (0.51 g) were added and the temperature was raised to 80° C. and held for 5.5 hours. Water (316 g) was added and agitation continued for 30 minutes before settling and separating the aqueous layer. Analysis of the MIBK solution revealed a 91.8% yield of methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin).

Aufarbeitung

  1. temperaturethe temperature was raised to 80° C.
  2. waitagitation continued for 30 minutes
  3. customseparating the aqueous layer

Quellen und Nachweise

ORD-Eintrag
ord-b5cdd34b6a204670a48e6bbc6c3770e9
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124761B2

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