Acetic Acid → HCID 13785423, compound

HRID 1905662Notes

Reaction equation

HRID 1905662 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].[C:6]([O:11]C)(=O)[C:7]([CH3:9])=[O:8].C(O)(=O)C>O>[OH:8][C:7]1([CH3:9])[N:2]([CH3:1])[C:3](=[O:4])[NH:5][C:6]1=[O:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11719MethylureaHCID 11748Methyl pyruvate

Product 1

HCID 13785423HCID 13785423, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

155 g of N-methylurea were added to 214 g of methyl pyruvate in a 3 1 eggplant type flask. 800 ml of acetic acid and 200 ml of water were added to dissolve them and the solution was refluxed for 2.5 hours. Then, the reaction mixture was evaporated to dryness and acetic acid was removed by azeotropic distillation with toluene. The obtained crude product was purified by chromatography on silica gel (ethyl acetate and 5% methanol/chloroform) to give 95 g of 5-hydroxy-1,5-dimethylhydantoin (compound 10).

Workup

  1. dissolutionto dissolve them
  2. temperaturethe solution was refluxed for 2.5 hours
  3. customThen, the reaction mixture was evaporated to dryness and acetic acid
  4. customwas removed by azeotropic distillation with toluene
  5. customThe obtained crude product
  6. customwas purified by chromatography on silica gel (ethyl acetate and 5% methanol/chloroform)

Sources & evidence

ORD record
ord-39c760cb752d42b59c8d8555620a26f9
Source dataset
uspto-grants-1987_03
Patent number
US04647574

Reaction notes

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