Butanal → 3-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]-5-butylidenehydantoin

HRID 357063Notes

Reaction equation

HRID 357063 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][NH:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:22](=O)[CH2:23][CH2:24][CH3:25].N1CCCC1>C(O)C>[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])[C:18](=[CH:22][CH2:23][CH2:24][CH3:25])[NH:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 261ButanalHCID 31268PyrrolidineHCID 189366653-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]hydantoin

Product 1

HCID 572685863-[4-(Imidazo[1,2-a]pyridin-5-ylthio)-butyl]-5-butylidenehydantoin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.00 g (3.29 mmol) of 3-[4-(imidazo-[1,2-a]pyridin-5-ylthio)butyl]hydantoin and 0.30 ml (3.29 mmol) of n-butyraldehyde in 10 ml of ethanol, 0.05 ml (0.6 mmol) of pyrrolidine was added, followed by refluxing for 16 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/ethanol=10/1→chloroform/methanol=10/1) to yield 0.43 g (36.5%, orange-yellow oily substance) of the desired product.

Workup

  1. temperatureby refluxing for 16 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, ethyl acetate/ethanol=10/1→chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-9195961baea547c89eb13b7921a96064
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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