4-Nitrobenzaldehyde → 5-(4-Nitrobenzylidene)-1,3-thiazolidine-2,4-dione

HRID 30642

Reaction equation

HRID 30642 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[S:12]1[CH2:16][C:15](=[O:17])[NH:14][C:13]1=[O:18].N1CCCCC1>C(O)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:16]2[S:12][C:13](=[O:18])[NH:14][C:15]2=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 5437ThiazolidinedioneHCID 8082Piperidine

Product 1

HCID 27682645-(4-Nitrobenzylidene)-1,3-thiazolidine-2,4-dioneYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-nitrobenzaldehyde (15.1 g), 1,3-thiazolidine-2,4-dione (11.70 g), piperidine (1.70 g) and ethanol (300 mL) was heated under reflux for 24 hrs. The reaction mixture was concentrated. The obtained residue was washed with ethanol to give 5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione as yellow crystals (14.8 g, yield 59%). Recrystallization thereof from acetone-hexane gave pale-yellow prism crystals. melting point: 272-273° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hrs
  3. concentrationThe reaction mixture was concentrated
  4. washThe obtained residue was washed with ethanol

Sources & evidence

ORD record
ord-02854ddf1583494d8386c11c20c29345
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

Loading…