5-[4-(2,4,5-Trimethyl-3,6-dimethoxyphenoxy)benzyl]thiazolidine-2,4-dione → 5-[4-(3,5,6-Trimethyl-1,4-benzoquinon-2-yloxy)benzyl]thiazolidine-2,4-dione

HRID 1742478Notes

Reaction equation

HRID 1742478 reaction equation
[CH3:1][C:2]1[C:22]([O:23]C)=[C:21]([CH3:25])[C:20]([CH3:26])=[C:19]([O:27]C)[C:3]=1[O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1>O.C(#N)C>[CH3:1][C:2]1[C:22](=[O:23])[C:21]([CH3:25])=[C:20]([CH3:26])[C:19](=[O:27])[C:3]=1[O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 190092435-[4-(2,4,5-Trimethyl-3,6-dimethoxyphenoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 152305155-[4-(3,5,6-Trimethyl-1,4-benzoquinon-2-yloxy)benzyl]thiazolidine-2,4-dioneYield 70.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2.1 g of ceric ammonium nitrate in a mixture of 2 ml of water and 2 ml of acetonitrile was added dropwise at 0° C. to a solution of 0.4 g of 5-[4-(2,4,5-trimethyl-3,6-dimethoxyphenoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Preparation 2) in 3 ml of acetonitrile, and the resulting mixture was stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed from the extract by distillation under reduced pressure, and the residue thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of benzene and ethyl acetate as the eluent, to give 260 mg of the title compound, melting at 153°-156° C. (with decomposition).

Workup

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed from the
  5. extractionextract by distillation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by column chromatography through silica gel
  8. additionby volume mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-169b3c1446aa42d58668b1020d7a0db3
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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