Ethyl chloroformate → 2-(4'-Fluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione

HRID 1449313Notes

Reaction equation

HRID 1449313 reaction equation
[CH3:1][NH:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)O)=[O:4].[OH-].[Na+].Cl[C:17]([O:19]CC)=[O:18]>O1CCOCC1>[F:13][C:10]1[CH:9]=[CH:8][C:7]([N:5]2[C:3](=[O:4])[N:2]([CH3:1])[C:17](=[O:18])[O:19]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 203490911-Methyl-3-(4'-fluorophenyl)-3-hydroxyurea

Product 1

HCID 203490922-(4'-Fluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Methyl-3-(4'-fluorophenyl)-3-hydroxyurea (10.0 g; 0.054 moles) was dissolved in dioxane (80 ml.) and mixed with a 2 N aqueous sodium hydroxide (32 ml; 0.064 mole). Ethyl chloroformate (5.7 ml; 0.06 mole) was added dropwise to the mixture at 10°-15° C. with stirring and the stirring continued for 1/2 hour after the addition was completed. The product which precipitated as formed was removed by filtration, washed with water and dried. The product was recrystallized from methanol and dried under vacuum to yield 2-(4'-fluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione as a solid melting 97°-99° C. and having the following elemental analysis as calculated for C9H7FN2O3 :

Workup

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

Sources & evidence

ORD record
ord-9802181b59f1489da1e3e940c18677b8
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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