Thiazolidinedione → 5-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione

HRID 4392

Reaction equation

HRID 4392 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].N1CCCCC1>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[C:28]2[S:24][C:25](=[O:30])[NH:26][C:27]2=[O:29])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Product 1

HCID 544863195-{4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedioneYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (5.0 g), 2,4-thiazolidinedione (3.8 g), piperidine (0.32 ml) and ethanol (100 ml) was stirred under reflux for 5 hours. After cooling, the crystals which separated out were collected by filtration to give 5-{4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene}-2,4-thiazolidinedione (5.1 g, 76.8%). Recrystallization from chloroform-ethanol afforded colorless needles, m.p. 213°-214° C. Elemental analysis for C22H18N2O4S, Calcd.: C, 65.01; H, 4.46; N, 6.89. Found: C, 64.81; H, 4.55; N, 6.78.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe crystals which separated out
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-512f61929c254761a4426dca28886965
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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