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Butanal → 5-Butylidene-3-[4-(2-methyl-imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357070
Notes
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Reaction equation

HRID 357070 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])[N:5]2[CH:22]=1.[CH:23](=O)[CH2:24][CH2:25][CH3:26].N1CCCCC1>C(O)C>[CH:23](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:6]2[N:5]3[CH:22]=[C:2]([CH3:1])[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=2)[C:19]1=[O:20])[CH2:24][CH2:25][CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 261ButanalHCID 8082PiperidineHCID 189368353-[4-(2-Methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Product 1

HCID 572386885-Butylidene-3-[4-(2-methyl-imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.67 g (2.0 mmol) of 3-[4-(2-methylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 0.18 ml (2.0 mmol) of n-butyraldehyde in 10 ml of ethanol, 0.02 ml (0.2 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 0.794 g (quant, 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 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-cc04a157cad04296a22e59f67f2b4123
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05840732

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes