Dichloromethane → 1,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-(2,2-dimethyl-3-chloropropionylmethoxy)pyrazole

HRID 2286485

Reaction equation

HRID 2286485 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:4]([CH3:18])=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([C:29]([CH3:33])([CH3:32])[CH2:30][Cl:31])=[O:28].C(Cl)Cl>C(C(C)=O)C>[CH3:1][N:2]1[C:6]([O:7][CH2:26][C:27](=[O:28])[C:29]([CH3:33])([CH3:32])[CH2:30][Cl:31])=[C:5]([C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:4]([CH3:18])=[N:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 104207672-Butanone, 1-bromo-4-chloro-3,3-dimethyl-HCID 178434070HCID 178434070, compound

Product 1

HCID 128800551,3-Dimethyl-4-(2,4-dichlorobenzoyl)-5-(2,2-dimethyl-3-chloropropionylmethoxy)pyrazoleYield 47.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Into a four necked flask was charged 1.0 g of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole, and the contents were dissolved in 20 ml of methyl ethyl ketone. 0.54 g of anhydrous potassium carbonate was added thereto, and 0.75 g of 1,1-dimethyl-2-chloroethyl bromomethyl ketone was further dropwise added while stirring whereby the mixture was reacted for 2 hours under the reflux condition (80° C.). After completion of the reaction, the reaction product was collected by filtration, and the solvent (methyl ethyl ketone) was distilled off to obtain a crude product. The crude product was passed through a silica gel column (eluent: methylene chloride), and the eluent was distilled off to obtain 0.7 g of the titled compound having a melting point of 58° to 60° C.

Workup

  1. customwas reacted for 2 hours under the reflux condition (80° C.)
  2. customAfter completion of the reaction
  3. filtrationthe reaction product was collected by filtration
  4. distillationthe solvent (methyl ethyl ketone) was distilled off
  5. customto obtain a crude product
  6. distillationthe eluent was distilled off

Sources & evidence

ORD record
ord-20cab9b218f0471ca8a5ec2629584746
Source dataset
uspto-grants-1981_05
Patent number
US04266963

Linked notes

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