Butanal → HCID 57237920, compound

HRID 357142Notes

Reaction equation

HRID 357142 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:21](=[O:22])[CH2:20][S:19][C:18]3=[O:23])(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:24](=O)[CH2:25][CH2:26][CH3:27].N1CCCCC1>C(O)C>[CH:24](=[C:20]1[S:19][C:18](=[O:23])[N:17]([CH2:16][CH2:15][CH2:14][CH2:13][S:10]([C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)(=[O:12])=[O:11])[C:21]1=[O:22])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 189367633-[4-(Imidazo[1,2-a]pyridin-5-ylsulfonyl)butyl]thiazolidine-2,4-dione

Product 1

HCID 57237920HCID 57237920, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.22 g (0.62 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylsulfonyl)butyl]thiazolidine-2,4-dione and 0.10 ml (1.1 mmol) of n-butyraldehyde in 5 ml of ethanol, 0.01 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 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=1/4) to yield 0.269 g (quant., 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 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=1/4)

Sources & evidence

ORD record
ord-1a4937614549496fa7485b2b8b88c5ac
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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