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Triethylamine → HCID 178428868, Verbindung

HRID 434214
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 434214
Br[C:2]1[C:3]([CH3:17])=[C:4]([C:12]2[CH2:16][CH2:15][O:14][N:13]=2)[C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:18][N:19]1[C:23]([OH:24])=[CH:22][CH:21]=[N:20]1.[C:25](=O)([O-])[O-:26].[K+].[K+].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:18][N:19]1[C:23]([OH:24])=[C:22]([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([C:12]3[CH2:16][CH2:15][O:14][N:13]=3)[C:3]=2[CH3:17])[CH:21]=[N:20]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 109470753-(3-Bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazoleHCID 178481816HCID 178481816, Verbindung

Produkt 1

HCID 178428868HCID 178428868, VerbindungAusbeute 11,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2.2 1 of 1,4-dioxane, 100 g (0.315 mol) of 3-(3-bromo-2-methyl-6-methylsulfonylphenyl)-4,5-dihydroisoxazole, 30.82 g (0.315 mol) of 1-methyl-5-hydroxypyrazole, 87 g (0.63 mol) of potassium carbonate, 63.5 g (0.63 mol) of triethylamine and 11.2 g (0.016 mol) of bis(triphenylphosphine)-palladium dichloride were added to a 3.5 l autoclave. The autoclave was then flushed twice with nitrogen, a carbon monoxide pressure of 10 kg/cm2 was applied and the mixture was heated with stirring to 130° C. The carbon monoxide pressure was increased to 20 kg/cm2 and the mixture was stirred at 130° C. for 24 h. The mixture was then concentrated under reduced pressure and the residue was taken up in water. The aqueous phase of pH 11 was extracted with dichloromethane. The organic phase is discarded. The aqueous phase is adjusted to pH 4 using 18% strength hydrochloric acid. The precipitate was filtered off, washed three times with water and dried at 40° C. under reduced pressure. This gives 85 g of product. The filtrate is extracted with dichloromethane. The organic phase is dried with sodium sulfate, and the solvent is then removed under reduced pressure, giving a further 12.7 g of product.

Aufarbeitung

  1. customThe autoclave was then flushed twice with nitrogen
  2. temperaturethe mixture was heated
  3. temperatureThe carbon monoxide pressure was increased to 20 kg/cm2
  4. stirringthe mixture was stirred at 130° C. for 24 h
  5. concentrationThe mixture was then concentrated under reduced pressure
  6. extractionThe aqueous phase of pH 11 was extracted with dichloromethane
  7. filtrationThe precipitate was filtered off
  8. washwashed three times with water
  9. customdried at 40° C. under reduced pressure
  10. extractionThe filtrate is extracted with dichloromethane
  11. dry with materialThe organic phase is dried with sodium sulfate
  12. customthe solvent is then removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9a8f131dd63d481abb09145d7effc1fa
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06670482B2

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