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

HRID 580254Notes

Reaction equation

HRID 580254 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].[CH3:16][C:17]([CH:19]([C:21]([CH3:23])=O)[CH3:20])=O.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:21]([CH3:23])=[C:19]([CH3:20])[C:17]([CH3:16])=[N:15]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 699493-Methyl-2,4-pentanedioneHCID 137982312-Fluoro-4-chloro-5-methylsulfonyloxyphenylhydrazine

Product 1

HCID 137982321-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,4,5-trimethylpyrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (2-fluoro-4-chloro-5-methylsulfonyloxyphenyl)hydrazine (25.5 g) of the formula: ##STR53## 3-methylpenta-2,5-dione (CH3COCH(CH3)COCH3) (11.4 g), ethanol (100 ml) and water (100 ml) was heated to reflux for one hour. After the reaction mixture was cooled, toluene was added thereto to form two layers. The toluene layer separated was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (29.3 g) as a pale yellow crystalline solid. Recrystallization of this solid from a mixture of n-hexane and ethyl acetate afforded a white crystalline solid. m.p. 123°-125° C.

Workup

  1. temperatureto reflux for one hour
  2. temperatureAfter the reaction mixture was cooled
  3. customto form two layers
  4. customThe toluene layer separated
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoval of the solvent
  8. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-d934f44226454b649bf88336f863f365
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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