Thiazolidinedione → HCID 86613935, compound

HRID 1811435Notes

Reaction equation

HRID 1811435 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH:17]=O)[C:8]2=[O:19])=[CH:4][CH:3]=1.[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28]>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH:17]=[C:26]3[S:22][C:23](=[O:28])[NH:24][C:25]3=[O:27])[C:8]2=[O:19])=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 5437ThiazolidinedioneHCID 866139161-(4-Chlorobenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde

Product 1

HCID 86613935HCID 86613935, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 1140TolueneSolvent

Procedure

1.50 g of 1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinolin-3-carboxaldehyde and 0.826 g of 2,4-thiazolidinedione were suspended in 30 ml of toluene, and five drops of piperidine and five drops of acetic acid were added, followed by heating and refluxing for 6 hours. The resultant was allowed to cool to precipitate a solid. The precipitated solid was collected by filtration and dried, giving 1.36 g of 5-[1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinolin-3-ylmethylidene]thiazolidine-2,4-dione as a yellow powder (68% yield).

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 6 hours
  3. temperatureto cool
  4. customto precipitate a solid
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-5dd811e5dc0645ff972e55ae72eb55a9
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

Loading…