Water → 4-Benzoyl-4-chloro-2,5-dimethyl-2,4-dihydro-3H-pyrazol-3-one

HRID 259052Notes

Reaction equation

HRID 259052 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([CH3:16])[NH:3]1.S(Cl)([Cl:20])(=O)=O.O>C1C=CC=CC=1>[CH3:1][N:2]1[C:6](=[O:7])[C:5]([Cl:20])([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4]([CH3:16])=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 499178HCID 499178, compound

Product 1

HCID 214226054-Benzoyl-4-chloro-2,5-dimethyl-2,4-dihydro-3H-pyrazol-3-oneYield 8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.16 g of 1,3-dimethyl-4-benzoyl-5-pyrazolone in 20 ml of dry benzene was added 1.62 g of sulfuryl chloride and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added to the reaction mixture and after shaking an organic layer was separated. The organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate and the solvent was distilled off from the solution. The so obtained residue was recrystallized from n-hexane to give 0.2 g of the desired product melting at 70.5° - 72° C. (Yield 7.6%)

Workup

  1. additionwas added to the reaction mixture
  2. stirringafter shaking an organic layer
  3. customwas separated
  4. washThe organic layer was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off from the solution
  7. customThe so obtained residue
  8. customwas recrystallized from n-hexane

Sources & evidence

ORD record
ord-4f5b2dcc8ea64e75918a5d4efbeecabb
Source dataset
uspto-grants-1977_07
Patent number
US04036631

Reaction notes

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