Methyl Isobutyl Ketone → Azoxystrobin

HRID 1645234

Reaktionsgleichung

Reaktionsgleichung von HRID 1645234
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[CH:24]([CH2:26][C:27]([CH3:29])=[O:28])[CH3:25].[C:30](=O)([O-])[O-].[K+].[K+].C1N2CC[N:38](CC2)[CH2:37]1>O>[C:37]([C:26]1[CH:24]=[CH:25][CH:30]=[CH:29][C:27]=1[O:28][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:38]

Komponenten

6

Edukt 4

HCID 7909Methyl Isobutyl KetoneHCID 9237DabcoHCID 11430Potassium CarbonateHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Produkt 1

HCID 3034285AzoxystrobinAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

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 (214 g), and heated to 45-50° C. 2-cyanophenyl (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 at this temperature for 4.5 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 97.2% 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-c00619b0959b4581be75fdba65f25472
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124761B2

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