Potassium Carbonate → 1,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-(4-methylbenzoylmethoxy) pyrazole

HRID 904052Notes

Reaction equation

HRID 904052 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](=[O:15])[CH2:13]Br)=[CH:10][CH:9]=1.[CH3:18][N:19]1[C:23]([OH:24])=[C:22]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[C:21]([CH3:35])=[N:20]1>C(C(C)=O)C.C(Cl)Cl>[CH3:18][N:19]1[C:23]([O:24][CH2:13][C:12](=[O:15])[C:11]2[CH:16]=[CH:17][C:8]([CH3:7])=[CH:9][CH:10]=2)=[C:22]([C:25](=[O:34])[C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[C:21]([CH3:35])=[N:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 692722-Bromo-4'-methylacetophenoneHCID 178434070HCID 178434070, compound

Product 1

HCID 131013251,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-(4-methylbenzoylmethoxy) pyrazoleYield 68.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a four necked flask, 2 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxy pyrazole was dissolved in 35 ml of methyl ethyl ketone, and 2 g of anhydrous potassium carbonate was added to the solution and 1.4 g of 4-methylphenacyl bromide was added dropwise to the mixture under stirring. The reaction was carried out for 2 hours under refluxing. The reaction mixture in the flask was cooled and filtered and methyl ethyl ketone was distilled off to obtain the precipitate of the reaction product. The precipitate was dissolved in methylene chloride and the solution was sequentially washed with water, an aqueous solution of sodium bicarbonate and water, and after drying over anhydrous sodium sulfate, methylene chloride was distilled off from the solution to obtain a crude product. The product was separated by a silica gel column with developing solvent (CH2Cl2 : 99.5% C2H5OH=100: 3) to obtain 1.87 g of brown oily product of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-(4-methyl benzoylmethoxy) pyrazole.

Workup

  1. additionwas added dropwise to the mixture
  2. temperatureunder refluxing
  3. temperatureThe reaction mixture in the flask was cooled
  4. filtrationfiltered
  5. distillationmethyl ethyl ketone was distilled off
  6. customto obtain the precipitate of the reaction product
  7. washthe solution was sequentially washed with water
  8. dry with materialan aqueous solution of sodium bicarbonate and water, and after drying over anhydrous sodium sulfate, methylene chloride
  9. distillationwas distilled off from the solution
  10. customto obtain a crude product
  11. customThe product was separated by a silica gel column with developing solvent (CH2Cl2 : 99.5% C2H5OH=100: 3)

Sources & evidence

ORD record
ord-40bc77bc8aef4cd0bb5cd30ac1ebd604
Source dataset
uspto-grants-1980_10
Patent number
US04230481

Reaction notes

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