Hydrochloric Acid → 5-Phenyl-1,2-oxazol-3-amine

HRID 884519

Reaktionsgleichung

Reaktionsgleichung von HRID 884519
S(O)(O)(=O)=O.[NH2:6]O.[O:8]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][C:11]#[N:12].[OH-].[Na+].Cl>O.CCO>[C:13]1([C:9]2[O:8][N:12]=[C:11]([NH2:6])[CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 64799BenzoylacetonitrileHCID 159255Hydroxylamine, sulfate (1:1)

Produkt 1

HCID 36207925-Phenyl-1,2-oxazol-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Hydroxylamine sulfate (2.5 g, 30.3 mmol) is added to a stirred solution of 3-oxo-3-phenylpropanenitrile (4 g, 27.6 mmol) and NaOH (1.27 g, 31.7 mmol) in H2O (25 mL)/EtOH (25 mL). The mixture is stirred at rt and then heated to 80° C. for 22 h. At this point, conc. HCl (3.39 ml, 41.3 mmol) is added and the mixture heated at 80° C. for an additional 2 h. It is then basified to pH 10 and extracted with EtOAc to give 5-phenyl-isoxazol-3-ylamine. MS (ESI) m/z 161.2 (M+1).

Aufarbeitung

  1. temperatureheated to 80° C. for 22 h
  2. temperaturethe mixture heated at 80° C. for an additional 2 h
  3. extractionextracted with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-7890fc6d5a6649119dd15c39a1173952
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242125B2

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