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

HRID 2274337Notes

Reaction equation

HRID 2274337 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-86dbc7f244d24bb8b1d282a8c1ca401d
Source dataset
uspto-grants-2015_09
Patent number
US09126959B2

Reaction notes

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