(5-Chloro-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone → HCID 178434085, compound

HRID 443689Notes

Reaction equation

HRID 443689 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17].[SH2:19].[Na]>C(O)C>[CH3:7][N:6]1[C:2]([SH:19])=[C:3]([C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:4]([CH3:8])=[N:5]1

Participants

4

Reactant 2

HCID 13020365(5-Chloro-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanoneHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178434085HCID 178434085, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.3 g. of 5-chloro-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole, 2.1 g. of sodium hydrogen sulfide 2 hydrate and 6 ml. of ethanol is heated under reflux on a water bath for 3 hours. After completion of the reaction, the ethanol is distilled off under reduced pressure from the reaction mixture and 15 ml. of water is added followed by extraction with benzene. To an aqueous layer is added conc. hydrochloric acid to adjust the pH to 1 and the mixture is extracted with chloroform. The extract is washed with water and then dried over anhydrous sodium sulfate. The solvent is distilled off from the extract to give the crude crystalline substance, which is then recrystallized from n-hexane to give 0.10 g. of the desired product as yellow powders having a melting point of 85°-86° C. Yield 33.3%.

Workup

  1. additionA mixture of 0.3 g
  2. temperatureunder reflux on a water bath for 3 hours
  3. customAfter completion of the reaction
  4. distillationthe ethanol is distilled off under reduced pressure from the reaction mixture and 15 ml
  5. additionof water is added
  6. extractionfollowed by extraction with benzene
  7. additionTo an aqueous layer is added conc. hydrochloric acid
  8. extractionthe mixture is extracted with chloroform
  9. washThe extract is washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent is distilled off from the
  12. extractionextract
  13. customto give the crude crystalline substance, which
  14. customis then recrystallized from n-hexane
  15. customto give 0.10 g

Sources & evidence

ORD record
ord-c62945d07d4543b7ba8e25eb7925a2a7
Source dataset
uspto-grants-1981_04
Patent number
US04261729

Reaction notes

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