Butanal → 5-Butylidene-3-(imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione

HRID 357059Notes

Reaction equation

HRID 357059 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([CH2:10][N:11]3[C:15](=[O:16])[CH2:14][S:13][C:12]3=[O:17])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:18](=O)[CH2:19][CH2:20][CH3:21].N1CCCCC1>C(O)C>[CH:18](=[C:14]1[S:13][C:12](=[O:17])[N:11]([CH2:10][C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)[C:15]1=[O:16])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 189368603-(Imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione

Product 1

HCID 572845405-Butylidene-3-(imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 223 mg (0.9 mmol) of 3-(imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione and 0.09 ml (1.0 mmol) of n-butyraldehyde in 5 ml of ethanol, 0.001 ml (0.1 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 water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/4) to yield 222 mg (82.2%, light yellow oily 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 water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, hexane/ethyl acetate=1/4)

Sources & evidence

ORD record
ord-7f2d08878ffa4385aea68ddacfdaeb82
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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