Thiazolidinedione → 5-(3,4-Dibromobenzylidene)thiazolidine-2,4-dione

HRID 1360986Notes

Reaction equation

HRID 1360986 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[Br:17])[CH:12]=O.N1CCCCC1>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[Br:17])[CH:12]=[C:5]1[S:1][C:2](=[O:7])[NH:3][C:4]1=[O:6]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 6220533,4-Dibromobenzaldehyde

Product 1

HCID 765458665-(3,4-Dibromobenzylidene)thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of thiazolidine-2,4-dione (90%, 65 mg, 0.5 mmol), 3,4-dibromobenzaldehyde (132 mg, 0.5 mmol), and piperidine (247 μL, 2.5 mmol) was shaken in acetic acid (2 mL) at 110° C. for 16 hours. After cooling, the mixture was concentrated to dryness in vacuo. The resulting crude product was shaken with water, centrifuged, and the supernatant was discarded. Subsequently the residue was shaken with ethanol, centrifuged, the supernatant was discarded and the residue was further evaporated to dryness to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to dryness in vacuo
  3. stirringSubsequently the residue was shaken with ethanol
  4. customthe residue was further evaporated to dryness

Sources & evidence

ORD record
ord-1368f77cd1ce4057b5c4f1e0728b3996
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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