Methyl Isobutyl Ketone → Azoxystrobin

HRID 1645233

Reaktionsgleichung

Reaktionsgleichung von HRID 1645233
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].C1N2CC[N:32](CC2)[CH2:31]1.[C:38](=O)([O-])[O-].[K+].[K+]>O>[C:31]([C:26]1[CH:24]=[CH:25][CH:38]=[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:32]

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 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (20 g at 97.1% strength; prepared as described in WO 92/08703) was added to MIBK (77 ml) and water (11 ml), followed by 2-cyanophenyl (8.0 g), DABCO (0.07 g) and potassium carbonate (14.1 g). The reaction was heated to 80° C. and monitored for the end of the reaction (complete after 8 hours). The reaction mixture was washed with water at 80° C. Analysis of the MIBK layer revealed a 95.7% yield of methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin).

Aufarbeitung

  1. custommonitored for the end of the reaction (complete after 8 hours)
  2. washThe reaction mixture was washed with water at 80° C

Quellen und Nachweise

ORD-Eintrag
ord-b0d822d89ec344f3bae619bea0e67e5e
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124761B2

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