2,4-Dichlorobenzoyl chloride → HCID 178456657, compound

HRID 1789242Notes

Reaction equation

HRID 1789242 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[CH2:7][C:6]([CH3:10])=[N:5]1)[CH:2]=[CH2:3].[OH-].[Ca+2].[OH-].[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>C(O)(C)C>[CH2:1]([N:4]1[C:8]([OH:9])=[C:7]([C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:15]=2[Cl:14])[C:6]([CH3:10])=[N:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 6093208Calcium HydroxideHCID 128940995-Methyl-2-(prop-2-en-1-yl)-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 178456657HCID 178456657, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 1.4 g. of 1-allyl-3-methyl-2-pyrazolin-5-one and 0.74 g. of calcium hydroxide in 20 ml. of isopropanol is heated under reflux with stirring for 1.5 hours. After cooling, to the resulting mixture is added dropwise 2.3 g. of 2,4-dichlorobenzoyl chloride. After completion of the dropwise addition, the resulting mixture is heated under reflux for 5.5 hours. After completion of the reaction, the solvent is distilled off from the reaction mixture and to the residue is added 3 ml. of 2N hydrochloric acid to adjust pH to 3.0. Then, the mixture is extracted with chloroform and the extract solvent is distilled off from the extract. The residue is dissolved in a small amount of benzene and the solution is washed with water, dried over anhydrous sodium sulfate and the solvent is distilled off. The resulting residue is recrystallized from isopropyl ether containing a small amount of methylene chloride to give 1.18 g. of the desired product as white crystals melting at 161°-163° C. Yield 40.7%.

Workup

  1. additionA suspension of 1.4 g
  2. temperatureunder reflux
  3. temperatureAfter cooling, to the resulting mixture
  4. additionis added dropwise 2.3 g
  5. additionAfter completion of the dropwise addition
  6. temperaturethe resulting mixture is heated
  7. temperatureunder reflux for 5.5 hours
  8. customAfter completion of the reaction
  9. distillationthe solvent is distilled off from the reaction mixture and to the residue
  10. additionis added 3 ml
  11. extractionThen, the mixture is extracted with chloroform
  12. distillationthe extract solvent is distilled off from the extract
  13. dissolutionThe residue is dissolved in a small amount of benzene
  14. washthe solution is washed with water
  15. dry with materialdried over anhydrous sodium sulfate
  16. distillationthe solvent is distilled off
  17. customThe resulting residue is recrystallized from isopropyl ether containing a small amount of methylene chloride
  18. customto give 1.18 g

Sources & evidence

ORD record
ord-5c5da0b5b6994d0ba89697fc67f6989a
Source dataset
uspto-grants-1987_08
Patent number
US04687858

Reaction notes

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