Propylamine → 5-(5-Chlorobenzoxazol-2-yl)-2-n-propylaminoaniline

HRID 74315

Reaktionsgleichung

Reaktionsgleichung von HRID 74315
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13](F)=[C:14]([N+:16]([O-])=O)[CH:15]=3)=[N:7][C:6]=2[CH:20]=1.C(N(CC)CC)C.[CH2:28]([NH2:31])[CH2:29][CH3:30].[H][H]>C(#N)C.[C].[Pd].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:31][CH2:28][CH2:29][CH3:30])=[C:14]([CH:15]=3)[NH2:16])=[N:7][C:6]=2[CH:20]=1

Komponenten

8

Edukt 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 674975535-Chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 674986575-(5-Chlorobenzoxazol-2-yl)-2-n-propylaminoanilineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 5-chloro-2-(2-fluoronitrobenzen-5-yl)benzoxazole (see Working Example 100-1) (1.5 g, 5.13 mmol) in acetonitrile (10 mL) was added triethylamine (779 mg, 7.70 mmol) and propylamine (364 mg, 6.16 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 solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL) was added 10% palladium-carbon (200 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 18 hours. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (1.5 g, 97% yield) as orange crystals.

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 solution of the crystals obtained in ethanol/tetrahydrofuran (1:2, 15 mL)
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-1f02076f3e574d15a642b8b62727a875
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829035B2

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