Hydrochloric Acid → 3-Isoxazolamine, 5-(1,1-dimethylethyl)-

HRID 127718

Reaktionsgleichung

[C:1]([CH2:7][C:8]#[N:9])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].S(O)(O)(=O)=O.[NH2:17]O.Cl>O.[OH-].[Na+]>[NH2:9][C:8]1[CH:7]=[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])[O:6][N:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of pivaloylacetonitrile (25.03 g) and 48% sodium hydroxide (18.16 g) in water (319 ml) is added a solution of hydroxylamine sulfate (18.06 g) in water (72 ml) and the mixture is adjusted to pH 8.10±0.05 with 5% sodium hydroxide (0.38 g), stirred at 60° C. for 18 hours, mixed with 36% hydrochloric acid (26.13 g) and stirred at 70° C. for 30 minutes. Then, 36% hydrochloric acid (40.31 g) is added to the reaction mixture, which is refluxed for 40 minutes under stirring. The mixture is evaporated under atmospheric pressure to recover pinacolone (1.07 g; yield, 5.3%) and cooled to ordinary temperature. After cooling, the reaction mixture is adjusted to pH 11.8 with 48% sodium hydroxide (58.08 g) and shaken with chloroform. The chloroform layer is washed with water and concentrated under reduced pressure to give 3-amino-5-t-butylisoxazole (23.80 g). Purity, 96.6%. Yield, 84.9%. No by-product, 3-(3-t-butyl-5-isoxazolyl)amino-5-t-butylisoxazole, is detected.

Aufarbeitung

stirringstirred at 70° C. for 30 minutes
temperatureis refluxed for 40 minutes
stirringunder stirring
customThe mixture is evaporated under atmospheric pressure
customto recover pinacolone (1.07 g; yield, 5.3%)
temperaturecooled to ordinary temperature
temperatureAfter cooling
stirringshaken with chloroform
washThe chloroform layer is washed with water
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-1ee6033f60f54e87a0f26d0d227abee1
Quelldatensatz: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04256899

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