Ammonium Hydroxide → 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile

HRID 2283872

반응식

HRID 2283872 반응식
P(Cl)(Cl)(Cl)=O.[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[N:21]=[C:20]([C:27]([NH2:29])=O)[CH:19]=2)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[NH4+]>>[C:6]1([S:12]([CH2:15][CH2:16][CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH2:25][CH3:26])[N:21]=[C:20]([C:27]#[N:29])[CH:19]=2)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

4

반응물 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 669590245-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide

생성물 1

HCID 669583215-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile수율 86.5%

반응 조건

온도
90 °C

실험 절차

Phosphorus oxychloride (25 mL) was added to 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide (10.4 g, 30.0 mmol) and heated to 90° C. for 2.5 hours. The reaction mixture was then cooled to ambient temperature and poured into ice water cooled by an ice bath. Additional ice was added to the reaction mixture and the pH of the mixture was adjusted to 8-9 by addition of 30% saturated aqueous ammonium hydroxide. The mixture was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 8.60 g of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile.

후처리

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. temperaturecooled by an ice bath
  3. additionAdditional ice was added to the reaction mixture
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d214c36ddab64c0a9eef407dd79fb50a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145410B2

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