Methanol → Methyl (2,5-dioxoimidazolidin-4-yl)acetate

HRID 1985114Notes

Reaction equation

HRID 1985114 reaction equation
[NH:1]1[CH:7]([CH2:8][C:9]([OH:11])=[O:10])[C:5](=[O:6])[NH:4][C:2]1=[O:3].OS(O)(=O)=O.[CH3:17]O>O>[CH3:17][O:10][C:9](=[O:11])[CH2:8][CH:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 95492Hydantoin-5-acetic acid

Product 1

HCID 5296047Methyl (2,5-dioxoimidazolidin-4-yl)acetateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Hydantoin acetic acid (20.57 g, 0.130 mol) in MeOH (210 mL) was treated with conc. H2SO4 (7 mL) and heated to reflux under N2 for 2.5 h. The resultant clear solution was cooled and the solvent removed in vacuo to give an oil which was diluted with water (65 mL) and extracted 4 times with EtOAc. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 19.81 g (88%) of (2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester. MS (ES+) Calc'd for C6H9N2O4 (M+1) 173. Found m/z 173 (100%). 1H NMR.

Workup

  1. temperatureheated
  2. temperatureto reflux under N2 for 2.5 h
  3. temperatureThe resultant clear solution was cooled
  4. customthe solvent removed in vacuo
  5. customto give an oil which
  6. extractionextracted 4 times with EtOAc
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-610a495051cd455b8a0ee57588eb776e
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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