Ethyl chloroformate → HCID 20349084, compound

HRID 1449311Notes

Reaction equation

HRID 1449311 reaction equation
[CH3:1][NH:2][C:3]([N:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1)O)=[O:4].[OH-].[Na+].Cl[C:20]([O:22]CC)=[O:21]>O1CCOCC1>[N+:14]([C:9]1[CH:8]=[C:7]([N:5]2[C:3](=[O:4])[N:2]([CH3:1])[C:20](=[O:21])[O:22]2)[CH:12]=[CH:11][C:10]=1[CH3:13])([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20349075HCID 20349075, compound

Product 1

HCID 20349084HCID 20349084, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Methyl-3-(3'-nitro-4'-methylphenyl)-3-hydroxyurea (11 g; 0.049 mole) was dissolved in dioxane (80 ml.) and mixed with a 2 N aqueous sodium hydroxide (28.5 ml; 0.057 mole). Ethyl chloroformate (5.2 ml; 0.054 mole) was added dropwise at 10°-15° C. with stirring and the stirring continued for about 1/2 hour after the addition was completed. The product which precipitated as formed was removed by filtration, washed with water and dried. This product was recrystallized from methanol and dried under vacuum to yield 2-(3'-nitro-4'-methylphenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione as yellow crystals melting 80°-81° C. and having the following elemental analysis as calculated for C10H9N3O5 :

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. customThis product was recrystallized from methanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-0e3864c6585648e9b5c2d60a43e5589e
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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