Thiazolidinedione → HCID 86758455, compound

HRID 2303823Notes

Reaction equation

HRID 2303823 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH2:25][O:26][C:27]4[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=4)[N:22]([CH3:35])[C:21]=3[CH:36]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[S:37]1[CH2:41][C:40](=[O:42])[NH:39][C:38]1=[O:43].N1CCCCC1>C(O)C>[C:12]([C:9]1[CH:8]=[C:7]([S:16][C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH2:25][O:26][C:27]4[CH:34]=[CH:33][C:30]([CH:31]=[C:41]5[S:37][C:38](=[O:43])[NH:39][C:40]5=[O:42])=[CH:29][CH:28]=4)[N:22]([CH3:35])[C:21]=3[CH:36]=2)[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86758456HCID 86758456, compound

Product 1

HCID 86758455HCID 86758455, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[6-(3,5-di-t-butyl-4-hydroxyphenylthio)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzaldehyde (502 mg), thiazolidine-2,4-dione (234 mg), piperidine (170 mg ) and ethanol (60 ml) was heated at reflux for 19 hours. The reaction mixture was evaporated to dryness and to the residue was added water and insoluble product was isolated by filtration and washed with water and diisopropyl ether to give the title compound (517 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19 hours
  3. customThe reaction mixture was evaporated to dryness and to the residue
  4. additionwas added water
  5. custominsoluble product was isolated by filtration
  6. washwashed with water and diisopropyl ether

Sources & evidence

ORD record
ord-07b31c56b06441588671b88ad89e46d2
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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