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Phenethylamine → 2-(2-(2-Phenylethyl)aminoanilin-5-yl)benzoxazole

HRID 74224
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74224
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(=O)([O-])[O-].[K+].[K+].[C:26]1([CH2:32][CH2:33][NH2:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H][H]>C(O)C.[C].[Pd].O>[C:26]1([CH2:32][CH2:33][NH:34][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])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 674988582-(2-(2-Phenylethyl)aminoanilin-5-yl)benzoxazoleAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390
HCID 178418390, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and 2-phenylethylamine (169 mg, 1.39 mmol), and this was heated to reflux for 4 hours. 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 tetrahydrofuran solution (5 mL) of the crystals obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 14 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 (143 mg, 37% yield).

Aufarbeitung

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (5 mL) of the crystals obtained
  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-6536a84f93fd4b59999079c975c027a0
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829035B2

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