Water → 1,3-Bis[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin

HRID 274726Notes

Reaction equation

HRID 274726 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[NH:16][C:15]2=[O:22])=[CH:5][CH:4]=1.Cl[CH2:24][CH2:25][CH2:26][CH2:27][S:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1.O>CN(C)C=O>[N:32]1[CH:33]=[CH:34][C:29]([S:28][CH2:27][CH2:26][CH2:25][CH2:24][N:16]2[C:17]([CH3:20])([CH3:21])[C:18](=[O:19])[N:14]([CH2:13][CH2:12][CH2:11][CH2:10][S:9][C:6]3[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=3)[C:15]2=[O:22])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 158169784-(4-Chlorobutylthio)pyridineHCID 190790983-[4-(4-Pyridylthio)butyl]-5,5-dimethylhydantoin

Product 1

HCID 190792051,3-Bis[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoinYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 96 mg (2.4 mmol) of 60% sodium hydride (oily) in 15 ml of dimethylformamide, 587 mg (2.0 mmol) of 3-[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin was added, and the mixture was stirred at room temperature for 10 minutes. To this reaction mixture, 807 mg (4.0 mmol) of 4-(4-chlorobutylthio)pyridine was added with stirring under ice-cooling, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the-solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to give 0.74 g of the desired product (80.7% yield, yellow oil).

Workup

  1. additionwas added
  2. stirringwith stirring under ice-
  3. temperaturecooling
  4. stirringthe mixture was stirred at 80° C. for 16 hours
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe extract was dried
  8. distillationthe-solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Sources & evidence

ORD record
ord-54962dc8a76047a986cc805ea9191051
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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