Thiazolidinedione → HCID 73889972, compound

HRID 1005915Notes

Reaction equation

HRID 1005915 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[CH3:8][N:9]([CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[C:10]1[N:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=2)[N:11]=1.C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[CH3:8][N:9]([CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([CH:30]=[C:5]2[S:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])=[CH:32][CH:33]=1)[C:10]1[N:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:17]=[CH:18][C:19]([NH2:20])=[CH:21][CH:22]=2)[N:11]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 3014295Piperidinium acetateHCID 22675140HCID 22675140, compound

Product 1

HCID 73889972HCID 73889972, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,4-thiazolidinedione (120 mg) and 4-[2-(N-methyl-N-(6-(4-anilinyl)pyrimidinyl)amino)ethoxy]benzaldehyde (280 mg) in a catalytic amount of piperidinium acetate containing toluene (60 mL), was stirred under reflux on a Dean-stark device for 4 hours. The resultant mixture was cooled and filtered. The filtered solid was dried to give the title compound (250 mg).

Workup

  1. temperatureunder reflux on a Dean-stark device for 4 hours
  2. filtrationfiltered
  3. customThe filtered solid was dried

Sources & evidence

ORD record
ord-db52b00ed3734b4b9a47e1d603c82476
Source dataset
uspto-grants-2004_09
Patent number
US06787551B2

Reaction notes

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