Thiazolidinedione → 5-{[2-(5-Ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione

HRID 377118Notes

Reaction equation

HRID 377118 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].N1CCCC[CH2:28]1>C(O)C>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12](=[C:24]2[S:20][C:21](=[O:26])[NH:22][C:23]2=[O:25])[C:19]2[CH:18]=[CH:15][CH:14]=[CH:13][CH:28]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 9881522Benzaldehyde, 4-[2-(5-ethyl-2-pyridinyl)ethoxy]-

Product 1

HCID 543911305-{[2-(5-Ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedioneYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde (2.40 g), 2,4-thiazolidinedione (1.66 g), ethanol (40 ml) and piperidine (0.2 ml) was heated under reflux for 8 hours. The resulting crystals were recrystallized form ethyl acetate to give 2.14 g (64%) of 5-{[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione as colorless crystals. m.p.: 165.5°-167° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. customThe resulting crystals were recrystallized form ethyl acetate

Sources & evidence

ORD record
ord-e6b3c5fa51314be2b32ec6a6f3cb6ea2
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Reaction notes

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