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Triethylamine → HCID 67497850, Verbindung

HRID 74289
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74289
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-])=O.C(N(CC)CC)C.[NH2:27][CH2:28][C:29]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:30].[H][H]>C(#N)C.[C].[Pd].O>[N:31]1([C:29]([CH2:28][NH:27][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[NH2:17])=[O:30])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 122918132-Amino-1-morpholinoethanoneHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67497850HCID 67497850, VerbindungAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390
HCID 178418390, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (1.20 g, 4.6 mmol) in acetonitrile (24 mL) was added triethylamine (1.17 g, 11.6 mmol) and aminoacetylmorpholine (0.73 g, 5.1 mmol), and this was heated to reflux for 3 h. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a solution of the residue obtained in methanol (40 mL) was added 10% palladium-carbon (120 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 3 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (1.50 g, 91% yield) as light brown crystals.

Aufarbeitung

  1. temperaturethis was heated
  2. temperatureto reflux for 3 h
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a solution of the residue obtained in methanol (40 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f6ff6c81e3c84026b2620a76bff1bddb
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829035B2

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