Butanal → 5-Butylidene-3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357081Notes

Reaction equation

HRID 357081 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]4[C:24](=[O:25])[CH2:23][S:22][C:21]4=[O:26])=[CH:13][CH:12]=[CH:11][N:10]3[CH:27]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:28](=O)[CH2:29][CH2:30][CH3:31].N1CCCCC1>C(O)C>[CH:28](=[C:23]1[S:22][C:21](=[O:26])[N:20]([CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[C:9]3[N:10]([CH:27]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[CH:11]=[CH:12][CH:13]=2)[C:24]1=[O:25])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 189368343-[4-(2-Phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Product 1

HCID 570498025-Butylidene-3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.91 g (5.0 mmol) of 3-[4-(2-phenylimidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 0.45 ml (5.0 mmol) of n-butyraldehyde in 20 ml of ethanol, 0.05 ml (0.5 mmol) of piperidine was added, followed by refluxing for 2 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1) to yield 1.70 g (78.0%, yellow foamy substance) of the desired product.

Workup

  1. temperatureby refluxing for 2 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-f3531fa6dabf46ce89e81508e2b714cc
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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