Ethanol → HCID 53716598, compound

HRID 357183Notes

Reaction equation

HRID 357183 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([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])=[CH:8][CH:7]=[CH:6][C:5]=12.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[CH2:28](O)C>>[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:9]2[N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=[CH:7][CH:8]=2)[C:19]1=[O:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 8082Piperidine2×HCID 189366943-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

Product 1

HCID 53716598HCID 53716598, compound

Procedure

To a solution of 1.61 g (5.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 0.54 g (5.0 mmol) of pyridine-2-a!aldehyde in 20 ml of ethanol, 0.05 ml (0.5 mmol) of piperidine was added, followed by refluxing for 6 hours. To the reaction mixture, 0.02 ml (0.2 mmol) of piperidine was added, followed by refluxing for 12 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, ethyl acetate) to yield 1.483 g (72.2%, light yellow crystal) of the desired product.

Workup

  1. temperatureby refluxing for 6 hours
  2. temperatureby refluxing for 12 hours
  3. temperatureAfter the reaction mixture was cooled
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with water
  7. customdried
  8. distillationafter which the solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-26e7fc6ebe9448b7a2e89f4610429755
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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