Hydrochloric Acid → HCID 20351906, compound

HRID 1077280Notes

Reaction equation

HRID 1077280 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([OH:13])[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:15](OCC)=[O:16].Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:10](=[O:11])[NH:12][C:15](=[O:16])[O:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 122169253,4-DICHLOROPHENYL HYDROXY UREA

Product 1

HCID 20351906HCID 20351906, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

1-(3,4-Dichlorophenyl)-1-hydroxyurea (6.0 grams) dissolved in aqueous sodium hydroxide (13 ml; 2.0 M) is charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 10° to 15°C and ethyl chloroformate (2.5 ml) is slowly added with stirring resulting in the formation of a white precipitate. After the addition is completed stirring is continued for a period of about 1/2 hour. After this time the reaction mixture is poured into a water-ice mixture and is treated with 6 N hydrochloric acid until the mixture is acidic. The solid product is then recovered by filtration and is dissolved in methylene chloride. The resulting solution is dried over anhydrous magnesium sulfate and is stripped of solvent. The remaining solid residue is then recrystallized from toluene to yield the desired product 2-(3,4-dichlorophenyl)-1,2,4-oxadiazolidin-3,5-dione having a melting point of 126° to 127.5°C.

Workup

  1. additionis charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. additionis slowly added
  4. customresulting in the formation of a white precipitate
  5. additionAfter the addition
  6. stirringis completed stirring
  7. filtrationThe solid product is then recovered by filtration
  8. dissolutionis dissolved in methylene chloride
  9. dry with materialThe resulting solution is dried over anhydrous magnesium sulfate
  10. customThe remaining solid residue is then recrystallized from toluene

Sources & evidence

ORD record
ord-232e3bad33cd4dc99ada00fdebfb4d36
Source dataset
uspto-grants-1976_05
Patent number
US03959478

Reaction notes

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