Ethyl chloroformate → HCID 20349076, compound

HRID 1449305Notes

Reaction equation

HRID 1449305 reaction equation
[CH2:1]([NH:3][C:4]([N:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[OH:7])=[O:5])[CH3:2].[OH-].[Na+].Cl[C:18](OCC)=[O:19]>>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([N:6]2[C:4](=[O:5])[N:3]([CH2:1][CH3:2])[C:18](=[O:19])[O:7]2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20349077HCID 20349077, compound

Product 1

HCID 20349076HCID 20349076, compound

Procedure

1-Ethyl-3-(4'-chlorophenyl)-3-hydroxyurea (8.0 g; 0.037 mole) prepared above was dissolved in cooled (10° C.) 2 N aqueous sodium hydroxide (21 ml.). Ethyl chloroformate (3.9 ml; 0.041 mole) was added dropwise at 10°-15° C. with stirring and the stirring was continued for about 1/2 hour after addition was completed. The desired compound precipitated as formed and was removed by filtration, washed with water, air dried, and recrystallized from methanol to yield solid 2-(4'-chlorophenyl)-4-ethyl-1,2,4-oxadiazolidine-3,5-dione as tan needle-like crystals melting 84°-86° C. and having the following elemental analysis as calculated for C10H9ClN2O3 :

Workup

  1. dissolutionabove was dissolved
  2. additionafter addition
  3. customThe desired compound precipitated
  4. customas formed
  5. customwas removed by filtration
  6. washwashed with water, air
  7. customdried
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5218accb6a24426c9ed678d32f39402b
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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