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

HRID 900026

Reaction equation

HRID 900026 reaction equation
[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

Participants

4

Reactant 3

HCID 64983-SulfoleneHCID 7516PhenylhydrazineHCID 14797Potassium Hydroxide

Product 1

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

Conditions

Temperature
60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-bbeafbfc484a4ef9983909737ecb41ef
Source dataset
uspto-grants-2008_04
Patent number
US07358014B2

Linked notes

Loading…