Ethyl chloroformate → 2-Phenyl-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione

HRID 267676

Reaction equation

HRID 267676 reaction equation
[F:1][C:2]([F:15])([F:14])[NH:3][C:4]([N:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7])=[O:5].[OH-].[Na+].Cl[C:19](OCC)=[O:20]>>[C:8]1([N:6]2[C:4](=[O:5])[N:3]([C:2]([F:14])([F:15])[F:1])[C:19](=[O:20])[O:7]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 215536781-Trifluoromethyl-3-phenyl-3-hydroxyurea

Product 1

HCID 215536942-Phenyl-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione

Procedure

1-Trifluoromethyl-3-phenyl-3-hydroxyurea (11 grams; 0.05 mol) is dissolved in a cooled (10°C) 2N aqueous sodium hydroxide solution (35 ml). Ethyl chloroformate (6 ml; 0.06 mol) is added dropwise at 10° to 15°C with stirring. Stirring is continued for a period of about 1/2 hour after the addition is completed resulting in the formation of a precipitate. The precipitate is recovered by filtration, washed with water and dried to yield 2-phenyl-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione.

Workup

  1. stirringStirring
  2. additionafter the addition
  3. customis completed resulting in the formation of a precipitate
  4. filtrationThe precipitate is recovered by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8c6a015cad7a4a71ab11bce0ca7d41a5
Source dataset
uspto-grants-1976_03
Patent number
US03944410

Linked notes

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