Sodium Hydroxide → 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid

HRID 1984470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984470
[OH-].[Na+].[C:3]1([S:9]([CH2:12][CH2:13][CH2:14][C:15]2[N:19]([CH2:20][CH2:21][CH2:22][CH3:23])[N:18]=[C:17]([C:24]([O:26]CC)=[O:25])[CH:16]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)C>[C:3]1([S:9]([CH2:12][CH2:13][CH2:14][C:15]2[N:19]([CH2:20][CH2:21][CH2:22][CH3:23])[N:18]=[C:17]([C:24]([OH:26])=[O:25])[CH:16]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 66959126ethyl 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylate

Produkt 1

HCID 669583705-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acidAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium hydroxide (12 mL, 6M) was added to a solution of ethyl 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylate (13.3 g, 35.1 mmol) in 100 mL of ethanol and heated to reflux overnight. The reaction mixture was concentrated under reduced pressure and the residue was diluted with 100 mL of water. The aqueous layer was extracted with several portions of ethyl acetate. The pH of the aqueous layer was adjusted to approximately 2-3 with aqueous hydrochloric acid and was then extracted with several portions of ethyl acetate. The combined organic layers originating from extraction of the aqueous layer were washed with brine, dried over magnesium sulfate, filtered, and concentrated to afford 10.5 g of 5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carboxylic acid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with 100 mL of water
  5. extractionThe aqueous layer was extracted with several portions of ethyl acetate
  6. extractionwas then extracted with several portions of ethyl acetate
  7. extractionThe combined organic layers originating from extraction of the aqueous layer
  8. washwere washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-49f1d00a98774c739332f8d8b54312d0
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544697B2

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