Ethanol → 1-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethylpyrazole

HRID 580271Notes

Reaction equation

HRID 580271 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:4][C:3]=1[NH:14][NH2:15].[C:16]([CH2:19][C:20](=O)[CH3:21])(=O)[CH3:17].C(O)C.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][S:10]([CH3:13])(=[O:11])=[O:12])=[CH:4][C:3]=1[N:14]1[C:20]([CH3:21])=[CH:19][C:16]([CH3:17])=[N:15]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 31261AcetylacetoneHCID 137982312-Fluoro-4-chloro-5-methylsulfonyloxyphenylhydrazine

Product 1

HCID 137982511-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethylpyrazoleYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-fluoro-4-chloro-5-methylsulfonyloxyphenylhydrazine (25.5 g), acetylacetone (10.0 g), ethanol (100 ml) and water (100 ml) was refluxed for 2 hours. After cooling, toluene was added to the reaction mixture to separate layers. The toluene layer as separated was washed with water and then subjected to distillation under a reduced pressure to remove the toluene, yielding the titled compound (29.3 g) as pale yellow crystals. Recrystallization from a mixture of hexane/ethyl acetate gave colorless crystals with melting point 77.5°-79° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling
  3. customto separate layers
  4. customThe toluene layer as separated
  5. washwas washed with water
  6. distillationsubjected to distillation under a reduced pressure
  7. customto remove the toluene

Sources & evidence

ORD record
ord-7557ff0cbeed440fbcd8174c36dba965
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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