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

HRID 1984472

Reaktionsgleichung

Reaktionsgleichung von HRID 1984472
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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 669583215-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrileAusbeute 86,5 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d0de6135e2b840c193e5370f695833ee
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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