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HRID 476610Notes

Reaction equation

HRID 476610 reaction equation
[CH:1](=[C:3]1[C:12](=[S:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:14])[CH:10]=2)O[CH:4]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2].[Se](=O)=O.[OH:24][OH:25].[OH2:26]>O1CCOCC1>[CH:1](=[C:3]1[C:12](=[S:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:14])[CH:10]=2)[O+:24](=[O:26])([O-:25])[CH:4]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:2]

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 24007Selenium DioxideHCID 86743548HCID 86743548, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1 g 3-ethylidene-6-methyl-thioflavanone, 100 mg selenium dioxide, 3.65 ml 30% hydrogen peroxide in 10 ml dioxane is warmed at 70° C. for 5 hours. Water is added and extraction with methylene chloride is followed by drying over magnesium sulfate and evaporation. The resulting white solid is purified by column chromatography over silicagel using methylene chloride as eluant. The best fractions are are mixed and recrystallised in a mixture of hexane and toluene. Pure 3-ethylidene-6-methyl-thioflavanone-1,1-dioxide is obtained as white crystals; m.p. 163°-174° C.

Workup

  1. extractionextraction with methylene chloride
  2. dry with materialby drying over magnesium sulfate and evaporation
  3. customThe resulting white solid is purified by column chromatography over silicagel
  4. additionThe best fractions are are mixed
  5. customrecrystallised in a mixture of hexane and toluene

Sources & evidence

ORD record
ord-d27febe1e34e4a57b9b5beeb25e29d15
Source dataset
uspto-grants-1989_12
Patent number
US04885298

Reaction notes

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