Potassium Carbonate → HCID 15916676, compound

HRID 904838Notes

Reaction equation

HRID 904838 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(OCC)(=O)C>[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

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12213214HCID 12213214, compound

Product 1

HCID 15916676HCID 15916676, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

21.3 g of 2-amino-4,5,6-trichlorophenol, 27.6 g of anhydrous potassium carbonate and 150 ml of ethyl acetate were placed in a 300 ml round-bottom flask and a solution of 9.9 g of diphosgen (trichloromethyl chloroformate) dissolved in 50 ml of ethyl acetate was added dropwise to the mixture with stirring under cooling on ice-water bath. The resulting mixture was heated at reflux temperature for one hour and the reaction solution was then cooled and subjected to suction filtration to remove insoluble salts. The filtrate was concentrated to dryness under reduced pressure to afford yellowish white crystals, which were recrystallized from methanol/acetone to give 19.6 g of 5,6,7-trichlorobenzoxazolone as white crystals with a melting point of 253°-254° C.

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder cooling on ice-water bath
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux temperature for one hour
  5. temperaturethe reaction solution was then cooled
  6. filtrationsubjected to suction filtration
  7. customto remove insoluble salts
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure
  9. customto afford yellowish white crystals, which
  10. customwere recrystallized from methanol/acetone

Sources & evidence

ORD record
ord-fdc086e61cb04c88a8a20dd22fa12313
Source dataset
uspto-grants-1983_12
Patent number
US04420486

Reaction notes

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