Ethyl chloroformate → HCID 20349086, compound

HRID 1449308Notes

Reaction equation

HRID 1449308 reaction equation
[CH3:1][NH:2][C:3]([N:5]([C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:8]=1[Cl:15])O)=[O:4].[OH-].[Na+].Cl[C:19]([O:21]CC)=[O:20]>O1CCOCC1>[Cl:15][C:8]1[CH:9]=[C:10]([Cl:14])[C:11]([Cl:13])=[CH:12][C:7]=1[N:5]1[C:3](=[O:4])[N:2]([CH3:1])[C:19](=[O:20])[O:21]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20349072HCID 20349072, compound

Product 1

HCID 20349086HCID 20349086, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Methyl-3-(2',4',5'-trichlorophenyl)-3-hydroxyurea (8 g; 0.03 mole) was dissolved in cooled (10° C.) 2 N aqueous sodium hydroxide solution (18 ml.) and mixed with dioxane (80 ml.). Ethyl chloroformate (3.3 ml; 0.034 mole) was added dropwise to the reaction mixture at 10°-15° C. with stirring. The stirring was continued for about 1/2 hour after the addition was completed. The dark, oily product was separated and recrystallized from methanol and boiled with powdered charcoal to yield 2-(2',4',5'-trichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione as tan needle-like crystals melting 112°-114° C. and having the following elemental analysis as calculated for C9H5Cl3N2O3 :

Workup

  1. additionafter the addition
  2. customThe dark, oily product was separated
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ba094d4432474785912658a8d7e91762
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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