3,4-Dichlorobenzaldehyde → 5-(4-(3,4-Dichlorobenzylideneamino)phenyl)thiazolidine-2,4-dione

HRID 1742827Notes

Reaction equation

HRID 1742827 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:19]=O>C(O)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH:19]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[S:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 227103,4-DichlorobenzaldehydeHCID 128509725-(4-Aminophenyl)thiazolidine-2,4-dione

Product 1

HCID 190060585-(4-(3,4-Dichlorobenzylideneamino)phenyl)thiazolidine-2,4-dioneYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into 20 ml of ethanol were suspended 0.50 g of 5-(4-aminophenyl)-thiazolidine-2,4-dione, and, after added 0.42 g of 3,4-dichlorobenzaldehyde thereto, the suspension was refluxed for 3 hours. After cooling by standing, the crystals deposited were collected by filtration. The crude crystals were recrystallized from ethanol to obtain 0.79 g of title compound.

Workup

  1. temperaturethe suspension was refluxed for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe crystals deposited were collected by filtration
  4. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-e9a02d51738344c3a0c7633f27cc843d
Source dataset
uspto-grants-1994_08
Patent number
US05342850

Reaction notes

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