Thiazolidinedione → 5-[(3-Phenoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 1360984Notes

Reaction equation

HRID 1360984 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].C([O-])(=O)C.[NH4+].[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)(=O)C>[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[C:5]1[S:1][C:2](=[O:7])[NH:3][C:4]1=[O:6])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 382843-PhenoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 28540035-[(3-Phenoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

A solution of thiazolidine-2,4-dione (90%, 78 mg, 0.6 mmol) and ammonium acetate (92 mg, 1.2 mmol) in acetic acid (1 mL) was added to 3-phenoxybenzaldehyde (52 μL, 0.6 mmol) and the resulting mixture was shaken at 115° C. for 16 hours. After cooling, the mixture was concentrated in vacuo to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ea3a5e1809b74e2e8c00deee8d274831
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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