Phosgene → HCID 15916676, compound

HRID 904837Notes

Reaction equation

HRID 904837 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[C:4]([Cl:10])[C:3]=1[OH:11].[C:12](=O)([O-])[O-:13].[K+].[K+].C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:8][C:6]1[C:5]([Cl:9])=[C:4]([Cl:10])[C:3]2[O:11][C:12](=[O:13])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 12213214HCID 12213214, compound

Product 1

HCID 15916676HCID 15916676, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

21.3 g of 2-amino-4,5,6-trichlorophenol, 27.6 g of anhydrous potassium carbonate and 150 ml of toluene were placed in a 300 ml round-bottom flask and 9.9 g of phosgen was slowly added to the mixture with stirring under cooling an ice-water bath. The resulting mixture was heated at reflux temperature for one hour and the reaction solution was then cooled and transferred to a 500 ml separating funnel. 150 ml of tetrahydrofuran and 150 ml of water were added into the funnel and the organic layer was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to remove the solvent, leaving yellowish white crystals. The crystals were recrystallized from a mixed solvent of methanol and acetone to give 22.7 g of 5,6,7-trichlorobenzoxazolone as white crystals having a melting point of 253°-254° C.

Workup

  1. temperatureunder cooling an ice-water bath
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux temperature for one hour
  4. temperaturethe reaction solution was then cooled
  5. customseparating funnel
  6. addition150 ml of tetrahydrofuran and 150 ml of water were added into the funnel
  7. customthe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated
  11. customto remove the solvent
  12. customleaving yellowish white crystals
  13. customThe crystals were recrystallized from a mixed solvent of methanol and acetone

Sources & evidence

ORD record
ord-587e9c034855457093b4cb55c3608ed4
Source dataset
uspto-grants-1983_12
Patent number
US04420486

Reaction notes

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