Acetic Acid → HCID 54432062, compound

HRID 1595489Notes

Reaction equation

HRID 1595489 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24][CH:23]=3)=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[S:30]1[CH2:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].N1CCCCC1.C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH:28]=[C:34]4[S:30][C:31](=[O:36])[NH:32][C:33]4=[O:35])=[CH:24][CH:23]=3)=[CH:17][CH:18]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21705012HCID 21705012, compound

Product 1

HCID 54432062HCID 54432062, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2 g (4.85 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl 4-methoxy-1-benzenesulfonate and 0.8 g (6.8 mmole) 2,4-thiazolidinedione, 0.4 g piperidine, 0.3 g acetic acid and 20 ml toluene was refluxed with water separation in a Dean-Stark apparatus for 2.5 hours. The solvent was evaporated in vacuo, the residue was dissolved in dichloromethane and washed with potassium hydrogensulfate solution and with water, dried with magnesium sulfate, filtered and the solvent was concentrated in vacuo. 1.2 g of crystals were filtered off and the mother liquid was purified by chromatography on silica gel using dichloromethane/diethylether (gradient) as eluent to give 0.5 g more, totally 1.7 g (yield 69%) of 5-(4-[2-(4-(4-methoxyphenylsulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with potassium hydrogensulfate solution and with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe solvent was concentrated in vacuo
  7. filtration1.2 g of crystals were filtered off
  8. customthe mother liquid was purified by chromatography on silica gel
  9. customto give 0.5 g more

Sources & evidence

ORD record
ord-ae92bcfc17d3437aac12ece3a0f4eb66
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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