Thiazolidinedione → 5-{4-[2-Hydroxy-2-(3-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dione

HRID 1873816Notes

Reaction equation

HRID 1873816 reaction equation
[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[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:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].N1CCCCC1>CCO>[OH:1][CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[C:25]2[S:21][C:22](=[O:27])[NH:23][C:24]2=[O:26])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 811336314-[2-Hydroxy-2-(3-methoxyphenyl)ethoxy]benzaldehyde

Product 1

HCID 866450765-{4-[2-Hydroxy-2-(3-methoxyphenyl)ethoxy]benzylidene}-1,3-thiazolidine-2,4-dioneYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 4-[2-hydroxy-2-(3-methoxyphenyl)ethoxy]benzaldehyde (1.76 g, 6.46 mmol) in absolute EtOH (50 ml) was added 2,4-thiazolidinedione (0.83 g, 7.11 mmol) and piperidine (0.70 mL, 7.11 mmol), and the resulting solution was heated to reflux. The reaction was refluxed overnight and then evaporated in vacuo. The residue was dissolved in EtOAc and this solution was washed with water (pH adjusted to ca. 5-6 with HOAc), brine, dried (Na2SO4), filtered and adsorbed onto silica gel. After chromatography with 20-30% EtOAc/DCM, the fractions containing compound were combined and evaporated in vacuo to give 1.38 g (58%) of the title compound as a yellow solid. MS (ESI−) for C19H17NO5S m/z 370.1 (M−H)−.

Workup

  1. temperaturethe resulting solution was heated to reflux
  2. temperatureThe reaction was refluxed overnight
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washthis solution was washed with water (
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. additionAfter chromatography with 20-30% EtOAc/DCM, the fractions containing compound
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-1153f501bed049d99d0b2f36e745985a
Source dataset
uspto-grants-2012_11
Patent number
US08304441B2

Reaction notes

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