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

HRID 267678Notes

Reaction equation

HRID 267678 reaction equation
[F:1][C:2]([F:16])([F:15])[NH:3][C:4]([N:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[OH:7])=[O:5].[OH-].[Na+].Cl[C:20](OCC)=[O:21]>O1CCOCC1>[F:14][C:11]1[CH:12]=[CH:13][C:8]([N:6]2[C:4](=[O:5])[N:3]([C:2]([F:15])([F:1])[F:16])[C:20](=[O:21])[O:7]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 215536861-Trifluoromethyl-3-(4'-fluorophenyl)-3-hydroxyurea

Product 1

HCID 215536762-(4'-Fluorophenyl)-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Trifluoromethyl-3-(4'-fluorophenyl)-3-hydroxyurea (11.9 grams; 0.05 mol) is dissolved in dioxane (80 ml) and mixed with 2N aqueous sodium hydroxide (30 ml). Ethyl chloroformate (5.7 ml; 0.06 mol) is then added dropwise to the mixture at 10° to 15°C, with stirring, resulting in the formation of a precipitate. The precipitate is recovered by filtration, washed with water and dried to yield 2-(4'-fluorophenyl)-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione.

Workup

  1. customresulting in the formation of a precipitate
  2. filtrationThe precipitate is recovered by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-8ee3bbf2e32642b08c6ac6ed648c5276
Source dataset
uspto-grants-1976_03
Patent number
US03944410

Reaction notes

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