Thiazolidinedione → 5-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

HRID 742608Notes

Reaction equation

HRID 742608 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]([CH:16]=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].N1CCCCC1>C(O)C>[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]([CH:16]=[C:24]3[S:20][C:21](=[O:26])[NH:22][C:23]3=[O:25])=[CH:14][CH:13]=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 533948925-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dioneYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 1.1 liter of ethanol was dissolved 94 g of 4-[2(5-ethyl-2-pyridyl) ethoxy]benzaldehyde (content 80.6%) obtained by substantially the same manner as b) of Example 1. To the solution were added 93.7 g of 2,4-thiazolidinedione and 19.7 g of piperidine, and the mixture was stirred for 5 hours under reflux. The reaction mixture was gradually cooled to room temperature. Resulting crystals were collected by filtration under reduced pressure, washed with 100 ml of ethanol and dried at 50° C. under reduced pressure to give 77.1 g of 5-[4-[2-(5-ethyl-2-pyridyl)ethoxy]benzilidene]-2,4-thiazolidinedione as pale yellow crystals (content 99.5%). [The yield based on 4-[2-(5-ethyl-2-pyridyl) ethoxy]benzaldehyde was 73.0%.] This product was in complete agreement with the authentic sample, 5-[4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene]-2,4-thiazolidinedione, in various spectrum data.

Workup

  1. customobtained by substantially the same manner as b) of Example 1
  2. temperatureunder reflux
  3. customResulting crystals
  4. filtrationwere collected by filtration under reduced pressure
  5. washwashed with 100 ml of ethanol
  6. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-4731ca02325649ce93eb938fecda639f
Source dataset
uspto-grants-1996_09
Patent number
US05554758

Reaction notes

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