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

HRID 377119Notes

Reaction equation

HRID 377119 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].N>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 222AmmoniaHCID 5437ThiazolidinedioneHCID 9881522Benzaldehyde, 4-[2-(5-ethyl-2-pyridinyl)ethoxy]-

Product 1

HCID 533948925-(4-(2-(5-Ethylpyridin-2-yl)ethoxy)benzylidene)thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde (27 g), ethanol (300 ml), 2,4-thiazolidinedione (33 g) and concentrated aqueous ammonia (14 ml) was heated under reflux for 5 hours. The precipitated crystals were separated. Recrystallization from 1,2-dichloroethane gave 21.6 g (57.6% of crystals of 5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzylidene}-2,4-thiazolidinedione.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe precipitated crystals were separated
  4. customRecrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-465f2299222b49309eb3c4b176997399
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Reaction notes

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