Ethyl chloroformate → HCID 4271757, compound

HRID 1449304Notes

Reaction equation

HRID 1449304 reaction equation
[CH3:1][NH:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)O)=[O:4].[OH-].[Na+].Cl[C:16]([O:18]CC)=[O:17]>>[C:7]1([N:5]2[C:3](=[O:4])[N:2]([CH3:1])[C:16](=[O:17])[O:18]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 22632Meturin

Product 1

HCID 4271757HCID 4271757, compound

Procedure

1-Methyl-3-phenyl-3-hydroxyurea (10 g; 0.06 mole) was dissolved in a cooled (10° C.) 2 N aqueous sodium hydroxide (0.068 mole) solution (34 ml.). Ethyl chloroformate (6.3 ml; 0.066 mole) was added dropwise at 10°-15° C. with stirring. The stirring was continued for about 1/2 hour after the addition was completed. The desired compound, which precipitated as formed, was removed by filtration, washed with water and dried. The compound was recrystallized from methanol and dried under vacuum to yield solid 2-phenyl-4-methyl-1,2,4-oxadiazolidine-3,5-dione having a melting point of 98°-99° C. and the following elemental analysis as calculated for C9H8N2O3 :

Workup

  1. additionafter the addition
  2. customThe desired compound, which precipitated
  3. customas formed
  4. customwas removed by filtration
  5. washwashed with water
  6. customdried
  7. customThe compound was recrystallized from methanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-89b8ce107ef045aa8f8ceca57cd0159a
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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