Hydrochloric Acid → HCID 21087498, compound

HRID 348432Notes

Reaction equation

HRID 348432 reaction equation
C([NH:9][C:10]1[NH:11][N:12]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=2[Cl:25])[C:13](=[O:16])[C:14]=1Br)(=O)C1C=CC=CC=1.[NH:26]1[CH:30]=[CH:29][CH:28]=[N:27]1.C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[OH-].[Na+].Cl>CO.CN1CCCC1=O>[NH2:9][C:10]1[NH:11][N:12]([C:17]2[C:18]([Cl:25])=[CH:19][C:20]([Cl:24])=[CH:21][C:22]=2[Cl:23])[C:13](=[O:16])[C:14]=1[N:26]1[CH:30]=[CH:29][CH:28]=[N:27]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1048PyrazoleHCID 14798Sodium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 17749109Barium hydroxide, octahydrateHCID 21087500HCID 21087500, compound

Product 1

HCID 21087498HCID 21087498, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
75 °C

Procedure

200 g of 3-benzoylamino-4-bromo-1-(2,4,6-trichlorophenyl)-5- pyrazolone, 59 g of pyrazol, 14 g of 2,6-di-t-butyl-p-cresol and 100 mL of N-methylpyrrolidone were mixed, and the resultant reaction mixture was heated at 75° C. under a nitrogen gas flow while agitated. The reaction mixture was cooled to 45° C., and 400 mL of methanol, 25 g of barium hydroxide octahydrate and 138 g of a 25% (W/V) aqueous solution of sodium hydroxide were added to the reaction mixture. The resultant mixture was agitated for six hours at an internal temperature of 65° C. After the reaction mixture was cooled to 45° C., 500 mL of concentrated hydrochloric acid were added to the mixture, and precipitated insoluble substances (barium chloride and sodium chloride) were eliminated by filtration. The filtrate was extracted twice with toluene, and the aqueous phase after the extraction was neutralized by adding a 25% (W/V) aqueous solution of sodium hydroxide so that the pH value of the aqueous phase became 3.5. Precipitated crystals were separated by filtration, and the obtained crystals were washed and dried to obtain 109 g of desired 3-amino-4-(1-pyrazolyl)-1-(2,4,6-trichlorophenyl)-5-pyrazolone (yield: 73.3%) as gray-white powder.

Workup

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to 45° C.
  3. temperatureAfter the reaction mixture was cooled to 45° C.
  4. customprecipitated insoluble substances (barium chloride and sodium chloride)
  5. filtrationwere eliminated by filtration
  6. extractionThe filtrate was extracted twice with toluene
  7. extractionthe aqueous phase after the extraction
  8. additionby adding a 25% (W/V) aqueous solution of sodium hydroxide so that the pH value of the aqueous phase
  9. customPrecipitated crystals
  10. customwere separated by filtration
  11. washthe obtained crystals were washed
  12. customdried

Sources & evidence

ORD record
ord-11e9133ea9b44eadba72476516c49777
Source dataset
uspto-grants-2007_02
Patent number
US07176321B2

Reaction notes

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