Hydrochloric Acid → HCID 21087498, compound

HRID 348431Notes

Reaction equation

HRID 348431 reaction equation
C([NH:9][C:10]1[NH:11][N:12]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=2[Cl:29])[C:13](=[O:20])[C:14]=1[N:15]1[CH:19]=[CH:18][CH:17]=[N:16]1)(=O)C1C=CC=CC=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[OH-].[Na+].Cl>CO>[NH2:9][C:10]1[NH:11][N:12]([C:21]2[C:22]([Cl:29])=[CH:23][C:24]([Cl:28])=[CH:25][C:26]=2[Cl:27])[C:13](=[O:20])[C:14]=1[N:15]1[CH:19]=[CH:18][CH:17]=[N:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17749109Barium hydroxide, octahydrateHCID 21087499HCID 21087499, compound

Product 1

HCID 21087498HCID 21087498, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

194 g of 3-benzoylamino-4-(1-pyrazolyl)-1-(2,4,6-trichlorophenyl)-5-pyrazolone were mixed with 400 mL of methanol, and 30 g of barium hydroxide octahydrate and 140 g of a 25% (W/V) aqueous solution of sodium hydroxide were added to the resultant mixture. After agitation of the resultant reaction mixture for 6 hours at an internal temperature of 65° C., the residual ratio of the raw material was 0.5% or less in an HPLC analysis. After the reaction mixture was cooled to 45° C., 500 mL of concentrated hydrochloric acid were added to the reaction 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 105 g of desired 3-amino-4-(1-pyrazolyl)-1-(2,4,6-trichlorophenyl)-5-pyrazolone (yield of 70.5%) as gray-white powder. The structure of the product was confirmed by 1H-NMR. Results of physical analyses are as follows.

Workup

  1. customAfter agitation of the resultant reaction mixture for 6 hours at an internal temperature of 65° C.
  2. customprecipitated insoluble substances (barium chloride and sodium chloride)
  3. filtrationwere eliminated by filtration
  4. extractionThe filtrate was extracted twice with toluene
  5. extractionthe aqueous phase after the extraction
  6. additionby adding a 25% (W/V) aqueous solution of sodium hydroxide so that the pH value of the aqueous phase
  7. customPrecipitated crystals
  8. customwere separated by filtration
  9. washthe obtained crystals were washed
  10. customdried

Sources & evidence

ORD record
ord-bf45b6a1f422479a84a119c62e08eb7d
Source dataset
uspto-grants-2007_02
Patent number
US07176321B2

Reaction notes

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