Thiazolidinedione → 2-[3-[(2,4-Dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetic acid

HRID 1360997Notes

Reaction equation

HRID 1360997 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[CH:8]([C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH2:14][C:15]([OH:17])=[O:16])=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[O:7]=[C:2]1[NH:3][C:4](=[O:6])[C:5](=[CH:8][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[O:13][CH2:14][C:15]([OH:17])=[O:16])[S:1]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 517045Sodium AcetateHCID 6018952-(3-Formylphenoxy)acetic acid

Product 1

HCID 47676012-[3-[(2,4-Dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]acetic acidYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Thiazolidine-2,4-dione (3.9 g, 33 mmol), 3-formylphenoxyacetic acid (6.0 g, 33 mmol), anhydrous sodium acetate (13.6 g, 165 mmol) and acetic acid (100 mL) was refluxed for 16 h. After cooling, the mixture was filtered and washed with acetic acid and water. Drying in vacuo afforded 5.13 g (56%) of [3-(2,4-dioxothiazolidin-5-ylidenemethyl)phenoxy]acetic acid as a solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washwashed with acetic acid and water
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-11134981278d496c8216f64a9689da0f
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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