Thiazolidinedione → HCID 86606235, compound

HRID 2426291Notes

Reaction equation

HRID 2426291 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:12][CH:13]=2)=[CH:5][CH:4]=1)=O.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[O:31]=[C:26]1[NH:27][C:28](=[O:30])[C:29](=[CH:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:10]=[C:11]([CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[S:12][CH:13]=3)=[CH:5][CH:4]=2)[S:25]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 86017444HCID 86017444, compound

Product 1

HCID 86606235HCID 86606235, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4 g (9 mmol) of N-[4-(4-formylphenyl)thiophen-2-ylmethyl]-N-methylbenzamide, 1.1 g (9 mmol) of 2,4-thiazolidinedione and 0.3 g (1.8 mmol) of piperidinium acetate in 40 ml of toluene is refluxed for 2 hours in a Dean-Stark system. The reaction medium is cooled and the precipitate is filtered off under vacuum. 3 g (78%) of N-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)phenyl]thiophen-2-ylmethyl}-N-methylbenzamide are obtained.

Workup

  1. temperatureThe reaction medium is cooled
  2. filtrationthe precipitate is filtered off under vacuum

Sources & evidence

ORD record
ord-940a999de730406aa6f857f6c887e0de
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

Loading…