Methylurea → NZ-419,5-HYDROXY-1-METHYLIMIDAZOLIDINE-2,4-DIONE

HRID 1905660Notes

Reaction equation

HRID 1905660 reaction equation
O.C(O[C:7](=[O:10])[CH:8]=[O:9])CCC.[CH3:11][NH:12][C:13]([NH2:15])=[O:14]>C(O)(=O)C>[OH:10][CH:7]1[N:12]([CH3:11])[C:13](=[O:14])[NH:15][C:8]1=[O:9]

Participants

4

Reactant 2

HCID 11719MethylureaHCID 18369960HCID 18369960, compound

Product 1

HCID 3036247NZ-419,5-HYDROXY-1-METHYLIMIDAZOLIDINE-2,4-DIONEYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15.0 g of glyoxylic acid n-butyl ester monohydrate and 7.4 g of N-methylurea were refluxed in an 80% aqueous solution of acetic acid for 1 hour. After the solvent was removed by distillation, a small amount of methanol was added to the residue and the insoluble matter was filtered off. The filtrate was then evaporated to dryness under reduced pressure. The resulting crude crystals were recrystallized from ethyl acetate to give 10.4 g of 5-hydroxy-1-methylhydantoin (compound 1) in the form of white crystals.

Workup

  1. customAfter the solvent was removed by distillation
  2. additiona small amount of methanol was added to the residue
  3. filtrationthe insoluble matter was filtered off
  4. customThe filtrate was then evaporated to dryness under reduced pressure
  5. customThe resulting crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-708161d77fa4431b84e73ac3b28550c2
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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