Thiazolidinedione → 5-[4-(2-Hydroxy-2-phenylethoxy)benzylidene]-1,3-thiazolidine-2,4-dione

HRID 1873802Notes

Reaction equation

HRID 1873802 reaction equation
[OH:1][C@@H:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[S:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[O:25].N1CCCCC1>CCO.C(O)(=O)C>[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:23]2[S:19][C:20](=[O:25])[NH:21][C:22]2=[O:24])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 866450714-[(2S)-2-hydroxy-2-phenylethoxy]benzaldehyde

Product 1

HCID 866450705-[4-(2-Hydroxy-2-phenylethoxy)benzylidene]-1,3-thiazolidine-2,4-dioneYield 86.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of 4-[(2S)-2-hydroxy-2-phenylethoxy]benzaldehyde (2.63 g, 10.8 mmol) in absolute EtOH (75 ml) was added 2,4-thiazolidinedione (1.27 g, 10.8 mmol) and piperidine (0.54 mL, 5.4 mmol), and the resulting solution was heated to reflux. The reaction was refluxed overnight. The reaction mixture was allowed to cool to RT. No precipitate formed. The pH of reaction mixture was ca. 5. Acetic acid (20 drops) was added. The reaction was evaporated in vacuo. The material was adsorbed onto silica gel and chromatographed eluting with 30-40% EtOAc/hexanes. Fractions containing product were combined and evaporated in vacuo to give 3.18 g (86%) of the title compound as a light yellow solid. MS (ESI−) for C18H15NO4S m/z 340.1 (M−H)−.

Workup

  1. temperaturethe resulting solution was heated to reflux
  2. temperatureThe reaction was refluxed overnight
  3. customNo precipitate formed
  4. customThe pH of reaction mixture
  5. customThe reaction was evaporated in vacuo
  6. customchromatographed
  7. washeluting with 30-40% EtOAc/hexanes
  8. additionFractions containing product
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5bc7a5063f514d158530c26784107b4c
Source dataset
uspto-grants-2012_11
Patent number
US08304441B2

Reaction notes

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