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Sodium hydride → HCID 86678203, Verbindung

HRID 1747552
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1747552
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=2)[N:3]=1.[F:16][C:17]([F:27])([F:26])[CH:18]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[OH:19].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[Cl:12][C:11]1[C:2]([O:19][CH:18]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[C:17]([F:16])([F:26])[F:27])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 6890902,3-Dichloro-6-nitroquinoxalineHCID 112175572,2,2-Trifluoro-1-(pyridin-3-yl)ethanol

Produkt 1

HCID 86678203HCID 86678203, VerbindungAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

In THF (200 mL) was dissolved 2,3-dichloro-6-nitroquinoxaline (4.00 g, 16.4 mmol) and the mixture was cooled to −78° C. To the solution were added 2,2,2-trifluoro-1-(pyridin-3-yl)ethanol (3.05 g, 17.2 mmol) obtained in Step 1 and sodium hydride (1.31 g, 32.8 mmol) and the mixture was stirred at −78° C. allowing the temperature to rise slowly to −30° C. over 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2) to give 3-chloro-6-nitro-2-(2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy) quinoxaline (3.98 g, 63% yield).

Aufarbeitung

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 3/2)

Quellen und Nachweise

ORD-Eintrag
ord-c60c47612e3343c6aa9a0d3d5a4fbb1a
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150569B2

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