Ammonium Chloride → 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide

HRID 1984471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984471
C(Cl)(=O)C(Cl)=O.[C:7]1([S:13]([CH2:16][CH2:17][CH2:18][C:19]2[N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=[C:21]([C:28]([OH:30])=O)[CH:20]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl-].[NH4+:32]>ClCCl.CN(C=O)C>[C:7]1([S:13]([CH2:16][CH2:17][CH2:18][C:19]2[N:23]([CH2:24][CH2:25][CH2:26][CH3:27])[N:22]=[C:21]([C:28]([NH2:32])=[O:30])[CH:20]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 669583705-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid

Produkt 1

HCID 669590245-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Oxalyl chloride (7.8 mL, 90.0 mmol) was added slowly via syringe to a solution of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid (10.5 g, 30.0 mmol) in 100 mL of dichloromethane containing one drop of DMF. After 2 hours of stirring, saturated ammonium chloride (100 mL) was added to the reaction mixture and the reaction was maintained for 1 hour. The reaction mixture was concentrated under reduced pressure, diluted with dichloromethane and washed with water. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 10.4 g of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxamide.

Aufarbeitung

  1. temperaturethe reaction was maintained for 1 hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with dichloromethane
  4. washwashed with water
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-90bd407d803d41cbb4ed419c69022936
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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