Phosphorus oxychloride → (5-Chloro-1-methyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone

HRID 637596Notes

Reaction equation

HRID 637596 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:8]=1[C:9]([C:11]1[CH:12]=[N:13][N:14]([CH3:17])[C:15]=1O)=[O:10]>>[Cl:6][C:7]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:8]=1[C:9]([C:11]1[CH:12]=[N:13][N:14]([CH3:17])[C:15]=1[Cl:3])=[O:10]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178481842HCID 178481842, compound

Product 1

HCID 13564076(5-Chloro-1-methyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanoneYield 98%

Procedure

To 5 ml of phosphorus oxychloride was added 2.71 g (0.01 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole and the resulting mixture was heated under reflux for 3 hours. After cooling, the reaction mixture was poured into ice water. Oily product was extracted with ethyl acetate, washed successively with 5% aqueous sodium bicarbonate and saturated brine and dried over anhydrous sodium sulfate. Then the solvent was distilled off therefrom under reduced pressure and the resulting oil was purified through silica gel column chromatography using benzene as an eluant to give 2.84 g of the title compound as pale yellow crystals, (yield: 98%), m.p. 81.0°-83.0° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionOily product was extracted with ethyl acetate
  5. washwashed successively with 5% aqueous sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen the solvent was distilled off
  8. customunder reduced pressure and the resulting oil was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-337af62e63fd4f1fa51e794a56d8febb
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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