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

HRID 127718

반응식

HRID 127718 반응식
[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

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 14798Sodium HydroxideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 159255Hydroxylamine, sulfate (1:1)

생성물 1

HCID 1714733-Isoxazolamine, 5-(1,1-dimethylethyl)-수율 123.3%

시약·촉매·용매 2

HCID 14798Sodium Hydroxide촉매HCID 962Water용매2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1ee6033f60f54e87a0f26d0d227abee1
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256899

연결된 노트

불러오는 중…