Dimethylhydantoin → 3-[4-(4-Pyridylthio)butyl]-5,5-dimethylhydantoin

HRID 274709Notes

Reaction equation

HRID 274709 reaction equation
[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].Cl[CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][C:2]1([CH3:9])[NH:6][C:5](=[O:7])[N:4]([CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:3]1=[O:8]

Participants

6

Reactant 4

HCID 6491DimethylhydantoinHCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 158169784-(4-Chlorobutylthio)pyridine

Product 1

HCID 190790983-[4-(4-Pyridylthio)butyl]-5,5-dimethylhydantoinYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.56 g (20 mmol) of 5,5-dimethylhydantoin and 4.03 g (20 mmol) of 4-(4-chlorobutylthio)pyridine in 20 ml of N,N-dimethylformamide, 3.00 ml (20 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at room temperature for 43 hours, followed by further stirring at 70° C. for 10 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed three times with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to give 3.33 g of the desired compound (56.8% yield, colorless crystals).

Workup

  1. stirringby further stirring at 70° C. for 10 hours
  2. washthe mixture was washed three times with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Sources & evidence

ORD record
ord-c6670226ee814f0fb72b279043da3c07
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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