Potassium Hydroxide → Pioglitazone

HRID 1743338Notes

Reaction equation

HRID 1743338 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[OH-].[K+].S(C1C=CC(C)=CC=1)(O[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH3:31])=[CH:26][N:25]=1)(=O)=O>C(O)C>[CH2:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][O:1][C:2]2[CH:15]=[CH:14][C:5]([CH2:6][CH:7]3[S:11][C:10](=[O:12])[NH:9][C:8]3=[O:13])=[CH:4][CH:3]=2)=[N:25][CH:26]=1)[CH3:31]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dioneHCID 112667342-(5-Ethyl-2-pyridyl)ethyl Tosylate

Product 1

HCID 4829Pioglitazone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g of 5-(4-hydroxybenzyl)-1,3-thiazolidine-2,4-dione is dissolved in ethanol (7 ml) with KOH (0.25 g) and mixed at room temperature for 2 hours. To the obtained salt 2-(5-ethyl-2-pyridyl)ethyl tosylate is added and the reaction mixture is refluxed for 5 hours. After cooling the precipitated salt is filtered off, pH is adjusted and the solvent is evaporated. The semi-solid residue is mixed in water and the solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off and recrystallized from the mixture DMF-water.

Workup

  1. additionmixed at room temperature for 2 hours
  2. temperaturethe reaction mixture is refluxed for 5 hours
  3. temperatureAfter cooling the precipitated salt
  4. filtrationis filtered off
  5. customthe solvent is evaporated
  6. additionThe semi-solid residue is mixed in water
  7. filtrationthe solid portion of 5-[[4-[2-(5-ethyl-2-pyridyl) ethoxy]phenyl]methyl]-2.4-thiazolidinedione (0.18 g) is filtered off
  8. customrecrystallized from the mixture DMF-water

Sources & evidence

ORD record
ord-a298d54cbbb64a5c853cf876265d4c22
Source dataset
uspto-grants-2006_03
Patent number
US07009057B2

Reaction notes

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