Reaction #58920

Reaction equation

4-nitrobenzaldehyde

1,3-thiazolidine-2,4-dione

piperidine

→

5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione

Yield 59.2%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 24 hrs
3. 3
   ConcentrationThe reaction mixture was concentrated
4. 4
   WashThe obtained residue was washed with ethanol

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.

Source