Thiazolidinedione → HCID 86645080, compound

HRID 2274347Notes

Reaction equation

HRID 2274347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:19])[CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].N1CCCCC1>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:19])[CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[C:24]3[S:20][C:21](=[O:26])[NH:22][C:23]3=[O:25])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86645079HCID 86645079, compound

Product 1

HCID 86645080HCID 86645080, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 4-[2-(3-chlorophenyl)-2-hydroxyethoxy]benzaldehyde (1.08 g, 3.90 mmol) in absolute EtOH (50 mL) was added 2,4-thiazolidinedione (0.50 g, 4.29 mmol) and piperidine (0.42 mL, 4.3 mmol), and the resulting solution was heated to reflux and then stirred overnight at room temperature. The reaction mixture was evaporated in vacuo and the residue was dissolved in EtOAc. This solution was washed with aqueous HOAc (pH 5-6), brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was adsorbed onto silica gel and chromatographed eluting with 10-20% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 1.31 g (89%) of the product as a light yellow solid. MS (ESI+) for C18H14ClNO4S m/z 375.0 (M+H)+. MS (ESI−) for C18H14ClNO4S m/z 374.1 (M−H)−.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux
  3. customThe reaction mixture was evaporated in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThis solution was washed with aqueous HOAc (pH 5-6), brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customchromatographed
  10. washeluting with 10-20% EtOAc/DCM
  11. additionFractions containing product
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-65dd232f782941199fec96da3c4f905d
Source dataset
uspto-grants-2015_09
Patent number
US09126959B2

Reaction notes

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