Water → HCID 67497897, Verbindung

HRID 74177

Reaktionsgleichung

Reaktionsgleichung von HRID 74177
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])O.[Na+].[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.O>C(O)C>[CH:25]1([NH:31][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7965CyclohexylamineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Produkt 1

HCID 67497897HCID 67497897, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.19 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (295 mg, 2.32 mmol) and cyclohexylamine (288 mg, 2.32 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and this was extracted with ethyl acetate. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crystals that were purified by silica gel column chromatography to yield the title compound (191 mg, 48% yield) as orange crystals.

Aufarbeitung

  1. temperaturethis was heated
  2. temperatureto reflux
  3. extractionthis was extracted with ethyl acetate
  4. customThe organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crystals that
  9. customwere purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-45e57a9ab34a4672953774b6c1da7524
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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