Tin tetrachloride → HCID 82468131, Verbindung

HRID 1508862

Reaktionsgleichung

Reaktionsgleichung von HRID 1508862
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C:9]2[O:10][CH:11]=[CH:12][N:13]=2)=[CH:6][CH:5]=1)([O-])=O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.[OH-].[Na+]>[O:10]1[CH:11]=[CH:12][N:13]=[C:9]1[CH2:8][C:7]1[CH:14]=[CH:15][C:4]([NH2:1])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 24287Tin tetrachlorideHCID 901105832-(4-Nitrobenzyl)oxazole

Produkt 1

HCID 82468131HCID 82468131, VerbindungAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-(4-nitrobenzyl)oxazole (0.108 g, 0.59 mmol) in ethanol (3 mL) was added tin chloride (0.531 g, 2.35 mmol) and the mixture was stirred at 50° C. for 3 h. After this time, the reaction mixture was cooled, diluted with 1M sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to afford the title compound (0.076 g, 63%) as a yellow oil. MW=174.20. 1H NMR (CD3OD, 500 MHz) δ 7.78 (d, J=0.8 Hz, 1H), 7.05 (d, J=0.8 Hz, 1H), 7.02-6.97 (m, 2H), 6.69-6.65 (m, 2H), 3.97 (s, 2H); APCI MS m/z 175 [M+H]+.

Aufarbeitung

  1. temperatureAfter this time, the reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7ecaa61db4b94a3287c53b43cfc33c08
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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