Sodium Hydroxide → 3,5-Bis(4-bromophenyl)isoxazole

HRID 1356881

Reaktionsgleichung

Reaktionsgleichung von HRID 1356881
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.[NH2:21]O.[OH-].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[O:18][N:21]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 1474381,3-Propanedione, 1,3-bis(4-bromophenyl)-HCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 122077563,5-Bis(4-bromophenyl)isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In a 250 ml round bottom flask, 4 g (10.4 mmol) of [2] was dissolved in 100 ml dry dioxane and heated to reflux, then 3.0 g (43.2 mmol) hydroxylamine hydrogen chloride in 10 ml water and 5 ml (25 mmol) 5 N NaOH was then dropped into the refluxing mixture. After 12 hours, the reaction mixture was cooled down to room temperature, and the solvent was removed in vacuo. The product was recrystallized from ethanol. Characterization. Yield: 3.41 g (85%). M.P. 218.5-219.5° C. 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.78(d, 2H, ArH), 7.74 (d, 2H, Ar′H), 7.66 (d, 2H, ArH), 7.62 (d, 2H, Ar′H), 6.82 (s, 1H, isoxazole proton). EI-MS: 379(M+), 224, 183, 155.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. customthe solvent was removed in vacuo
  4. customThe product was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a4fc42e5f37f43efab02ae67b7af7461
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586763B2

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