Thiazolidinedione → (5Z)-5-[(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methylene]-1,3-thiazolidine-2,4-dione

HRID 2221535Notes

Reaction equation

HRID 2221535 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].N1CCCCC1>C(O)C>[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[C:26]2/[C:25](=[O:27])[NH:24][C:23](=[O:28])[S:22]/2)=[CH:12][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 229307603-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 23076583(5Z)-5-[(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methylene]-1,3-thiazolidine-2,4-dioneYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-4-carbaldehyde (2.50 g), 1,3-thiazolidine-2,4-dione (1.05 g), piperidine (0.15 g) and ethanol (80 mL) was heated under reflux for 1 hr. The reaction mixture was concentrated, and the obtained crystals were washed with ethanol to give (5Z)-5-[(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)methylene]-1,3-thiazolidine-2,4-dione as yellow crystals (2.97 g, yield 87%). Recrystallization from tetrahydrofuran-hexane gave yellow prism crystals. melting point: >300° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. washthe obtained crystals were washed with ethanol

Sources & evidence

ORD record
ord-d431f948a09d4179ba4503327bfe171a
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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