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Dabco → Azoxystrobin

HRID 1645232
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1645232
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](=[O:26])([O-])[O-].[K+].[K+].C1N2[CH2:35][CH2:36][N:31](CC2)C1>CN(C=O)C>[C:36]([C:35]1[CH:11]=[CH:10][CH:9]=[CH:14][C:23]=1[O:26][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:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 3034285AzoxystrobinAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (96.2 g; prepared as described in WO 92/08703) in DMF (approximately 100 g) was added a DMF solution of 2-cyanophenyl (78.5 g at 50% w/w 2-cyanophenyl) followed by potassium carbonate (63.5 g) and DABCO (0.34 g). The mixture was heated to 80° C. and held for 75 minutes. The DMF was removed by vacuum distillation to a final temperature of 100° C. Toluene (165.8 g) was charged to the distillation residues and the temperature brought to 75° C. before adding hot water (318.6 g) and stirring for 30 minutes at 80° C. The aqueous phase was removed and then the toluene layer was sampled and analysed. The solution yield of methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin) was 90.0%. The toluene was distilled off under vacuum. Methanol (88 g) was added to the distillation residues at 70° C. and the mixture cooled to <5° C., filtered and the cake washed with methanol (2×30 ml) to give, after drying, methyl (E)-2-{2-[6-(2-cyano-phenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (83.2% yield).

Aufarbeitung

  1. customThe DMF was removed by vacuum distillation to a final temperature of 100° C
  2. additionToluene (165.8 g) was charged to the distillation residues
  3. custombrought to 75° C.
  4. additionbefore adding hot water (318.6 g)
  5. customThe aqueous phase was removed
  6. aliquotthe toluene layer was sampled
  7. distillationThe toluene was distilled off under vacuum
  8. additionMethanol (88 g) was added to the distillation residues at 70° C.
  9. temperaturethe mixture cooled to <5° C.
  10. filtrationfiltered
  11. washthe cake washed with methanol (2×30 ml)
  12. customto give
  13. customafter drying

Quellen und Nachweise

ORD-Eintrag
ord-06c8aa0c775c47019512e4f701262840
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124761B2

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