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

HRID 6185Notes

Reaction equation

HRID 6185 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-a61d1f22e885485180fc72a79cdacf3e
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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