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

HRID 267682Notes

Reaction equation

HRID 267682 reaction equation
[F:1][C:2]([F:16])([F:15])[NH:3][C:4]([N:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=1)[OH:7])=[O:5].[OH-].[Na+].Cl[C:20](OCC)=[O:21]>O1CCOCC1>[CH3:14][C:10]1[CH:9]=[C:8]([N:6]2[C:4](=[O:5])[N:3]([C:2]([F:15])([F:16])[F:1])[C:20](=[O:21])[O:7]2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 215536751-Trifluoromethyl-3-(3'-methylphenyl)-3-hydroxyurea

Product 1

HCID 215536962-(3'-Methylphenyl)-4-trifluoromethyl-1,2,4-oxadiazolidine-3,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Trifluoromethyl-3-(3'-methylphenyl)-3-hydroxyurea (11.7 grams; 0.05 mol) is dissolved in dioxane (75 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 with stirring, resulting in the formation of a precipitate. The precipitate is recovered by filtration, is washed and dried to yield 2-(3'-methylphenyl)-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. washis washed
  4. customdried

Sources & evidence

ORD record
ord-951276b8fa664734a398b48048bec027
Source dataset
uspto-grants-1976_03
Patent number
US03944410

Reaction notes

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