Ethyl chloroformate → HCID 20349095, compound

HRID 1449307Notes

Reaction equation

HRID 1449307 reaction equation
[CH2:1]([NH:4][C:5]([N:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[OH:8])=[O:6])[CH:2]=[CH2:3].[OH-].[Na+].Cl[C:19](OCC)=[O:20]>O1CCOCC1.O>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([N:7]2[C:5](=[O:6])[N:4]([CH2:1][CH:2]=[CH2:3])[C:19](=[O:20])[O:8]2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 20349082HCID 20349082, compound

Product 1

HCID 20349095HCID 20349095, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1-Allyl-3-(4'-chlorophenyl)-3-hydroxyurea (6.0 g.) was dissolved in cooled dioxane (50 ml.) and a solution of sodium hydroxide (1.3 g.) in water (15 ml.) was added thereto. Ethyl chloroformate (3.2 g; 2.9 ml.) was added dropwise at 10°-15° C. with stirring and the stirring continued for about 1/2 hour after the addition was completed. The reaction mixture was poured into cold water (300 ml.), stirred and filtered to separate the precipitate. The precipitate was recrystallized from ethanol and dried in vacuo at room temperature to yield 2-(4'-chlorophenyl)-4-allyl-1,2,4-oxadiazolidine-3,5-dione as white needle-like crystals melting 56°-57° C. and having the following elemental analysis as calculated for C11H9ClN2O3 :

Workup

  1. additionafter the addition
  2. stirringstirred
  3. filtrationfiltered
  4. customto separate the precipitate
  5. customThe precipitate was recrystallized from ethanol
  6. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-944bfe40a1ec4db3864af02ff8e1a5d2
Source dataset
uspto-grants-1980_02
Patent number
US04190431

Reaction notes

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