Thiazolidinedione → 4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoic acid methyl ester

HRID 416286Notes

Reaction equation

HRID 416286 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[S:13]1[CH2:17][C:16](=[O:18])[NH:15][C:14]1=[O:19].N1CCCCC1>COCCO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:17]2[S:13][C:14](=[O:19])[NH:15][C:16]2=[O:18])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 6060034-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoic acid methyl esterYield 35.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 4-formyl-benzoic acid methyl ester (1.0 g, 6.7 mmol), thiazolidine-2,4-dione (0.78 g, 6.7 mmol) and piperidine (0.66 ml, 6.7 mmol) in 2-methoxy-ethanol (20 ml) was refluxed for 2 hrs, cooled to the room temperature and evaporated. The residue was triturated with CH2Cl2 to produce a crystalline material which was collected by filtration to afford the title compound (620 mg, 35% yield). LRMS: 263.3 (calcd.), 264.1 [MH]+ (found).

Workup

  1. customevaporated
  2. customThe residue was triturated with CH2Cl2
  3. customto produce a crystalline material which
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b79b55086db64a34a6959ec638143baf
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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