Ethanol → 5-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione

HRID 377117Notes

Reaction equation

HRID 377117 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.[S:19]1[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[O:25].C(O)C.N1CCCCC1>C(O)(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[C:23]3[S:19][C:20](=[O:25])[NH:21][C:22]3=[O:24])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 14211280HCID 14211280, compound

Product 1

HCID 543908955-{4-[2-(6-Methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-[2-(6-methyl-2-pyridyl)ethoxy]benzaldehyde (1.21 g), 2,4-thiazolidinedione (0.59 g), ethanol (50 ml) and piperidine (0.33 g) was heated under reflux for 16 hours. The reaction mixture was poured into ice-water and acidified with acetic acid. The resulting crystals were collected by filtration to give 5-{4-[2-(6-methyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione. Yield: 1.34 g (78.5%). Recrystallization from methanol gave pale yellow prisms. m.p.: 180.5°-182° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1a6d81a3dd824440a25fbc6ea7f3219b
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Reaction notes

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