1,3-dimethyl-1H-pyrazol-5-ol → HCID 178434073, compound

HRID 1995810Notes

Reaction equation

HRID 1995810 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[NH:3]1.[OH-].[Ca+2].[OH-].[Cl:12][C:13]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>C(O)(C)C>[Cl:12][C:13]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[CH:18][C:14]=1[C:15]([C:5]1[C:4]([CH3:8])=[N:3][N:2]([CH3:1])[C:6]=1[OH:7])=[O:16]

Participants

5

Reactant 3

HCID 27668471,3-dimethyl-1H-pyrazol-5-olHCID 6093208Calcium HydroxideHCID 13235952HCID 13235952, compound

Product 1

HCID 178434073HCID 178434073, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

11.2 g (0.1 mole) of 1,3-dimethyl-5-pyrazolone and 9.6 g (0.13 mole) of calcium hydroxide were suspended in 165 ml of isopropanol, and with stirring, the suspension was heated under reflux for 30 minutes. The reaction mixture was cooled, and 22.4 g (0.1 mole) of 2,4-dichloro-3-methyl-benzoyl chloride was added dropwise. After the addition, the mixture was heated under reflux for 10 hours. The solvent was distilled off from the reaction mixture, and 40 ml of water was added. The mixture was acidified with 65 ml of 2 N hydrochloric acid, and extracted with 100 ml of chloroform twice. The extracts were washed with water, and dried over magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from toluene to give 14.9 g of colorless crystals (yield 49.8%; melting point 148.9°-149.5° C.).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe reaction mixture was cooled
  4. additionAfter the addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 10 hours
  7. distillationThe solvent was distilled off from the reaction mixture, and 40 ml of water
  8. additionwas added
  9. extractionextracted with 100 ml of chloroform twice
  10. washThe extracts were washed with water
  11. dry with materialdried over magnesium sulfate
  12. distillationThe solvent was distilled off
  13. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-154d1e56e5944adc86b8a0d6323c7960
Source dataset
uspto-grants-1983_09
Patent number
US04406688

Reaction notes

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