3-Sulfolene → 1-(1,1-Dioxothiolan-3-yl)-1-phenylhydrazine

HRID 900026

Reaktionsgleichung

Reaktionsgleichung von HRID 900026
[S:1]1([CH2:7][CH:6]=[CH:5][CH2:4]1)(=[O:3])=[O:2].[C:8]1([NH:14][NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[K+]>>[C:8]1([N:14]([CH:5]2[CH2:6][CH2:7][S:1](=[O:3])(=[O:2])[CH2:4]2)[NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

4

Edukt 3

HCID 64983-SulfoleneHCID 7516PhenylhydrazineHCID 14797Potassium Hydroxide

Produkt 1

HCID 28017481-(1,1-Dioxothiolan-3-yl)-1-phenylhydrazineAusbeute 53 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Butadiene sulfone (0.5 mol, obtained from Aldrich chemicals, Milwaukee, Wis.) and phenyl hydrazine (0.55 mol, 1.1 equiv. obtained from Aldrich Chemicals, Milwaukee, Wis.) were stirred for 5-10 minutes, and then 40% aqueous KOH solution (0.005 mol, 0.01 equiv. obtained from Aldrich Chemicals, Milwaukee, Wis.)) was added. The mixture was heated at 60° C. for 2 hours whereupon a solid separated. After 10 hours at room temperature, the solid was filtered, washed with excess of water and recrystallized from methanol to give the product as white crystals; yield 53%; mp 119.9-121.5° C.; 1H-NMR and 13C-NMR spectra in CDCl3 were in full agreement with the structure.

Aufarbeitung

  1. customseparated
  2. filtrationthe solid was filtered
  3. washwashed with excess of water
  4. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-bbeafbfc484a4ef9983909737ecb41ef
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358014B2

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