Ethanol → 5-[[2-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methylidene]-2,4-thiazolidinedione

HRID 2395693Notes

Reaction equation

HRID 2395693 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15][C:16]=2[CH3:17])=[N:7][CH:8]=1)=O.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].N1CCCCC1.C(O)C>O>[CH3:17][C:16]1[O:15][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:13][C:12]=1[CH2:11][CH2:10][O:9][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[C:28]2[S:24][C:25](=[O:30])[NH:26][C:27]2=[O:29])=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 185461516-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine-3-carbaldehyde

Product 1

HCID 539105175-[[2-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methylidene]-2,4-thiazolidinedioneYield 29.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (0.6 g), 2,4-thiazolidinedione (0.235 g), piperidine (0.066 ml) and ethanol (20 ml) was heated for 9 hours while refluxing. The reaction mixture was poured into water; the separating crystal, collected by filtration, was then recrystallized from ethanol-chloroform to yield 5-[[2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-pyridyl]methylidene]-2,4-thiazolidinedione (0.232 g, 29%) as a yellow crystal.

Workup

  1. temperaturewas heated for 9 hours
  2. temperaturewhile refluxing
  3. filtrationthe separating crystal, collected by filtration
  4. customwas then recrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-77c5322584f14d579e245f3b09231f43
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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