4-Toluenesulfonyl chloride → 5-Methoxy-1-methylimidazolidine-2,4-dione

HRID 1905661Notes

Reaction equation

HRID 1905661 reaction equation
[OH:1][CH:2]1[N:6]([CH3:7])[C:5](=[O:8])[NH:4][C:3]1=[O:9].[CH2:10](N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CO>[CH3:10][O:1][CH:2]1[N:6]([CH3:7])[C:5](=[O:8])[NH:4][C:3]1=[O:9]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 3036247NZ-419,5-HYDROXY-1-METHYLIMIDAZOLIDINE-2,4-DIONE2×

Product 1

HCID 123555505-Methoxy-1-methylimidazolidine-2,4-dioneYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g of 5-hydroxy-1-methylhydantoin (compound 1) were dissolved in absolute methanol and 6.7 g of triethylamine were added to the solution. 10.9 g (1.5 equivalent) of p-toluenesulfonyl chloride were then added to the solution, and was stirred at room temperature for 3 hours. After the reaction mixture was evaporated to dryness, a small amount of water was added to the residue and was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness, and the residue was purified by column chromatography on silica gel (ethyl acetate). The obtained crude compound was recrystallized from a mixture of ethyl acetate and hexane to give 3.8 g of 5-methoxy-1-methylhydantoin (compound 5) in the form of white crystals.

Workup

  1. customAfter the reaction mixture was evaporated to dryness
  2. additiona small amount of water was added to the residue
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate)
  7. customThe obtained crude compound
  8. customwas recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b2d47bb5f1874009a11ae347242dcdbb
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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