Potassium Carbonate → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

HRID 1462395Notes

Reaction equation

HRID 1462395 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[C:7]([CH3:13])=[N:8][N:9]([CH3:12])[C:10]=1[OH:11])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][N:28]([CH3:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[Cl:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[C:7]([CH3:13])=[N:8][N:9]([CH3:12])[C:10]=1[O:11][CH2:26][CH2:27][N:28]([CH3:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12522480N-(2-Bromoethyl)-N-methylanilineHCID 178434070HCID 178434070, compound

Product 1

HCID 132775064-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.85 g of 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-hydroxypyrazole was dissolved in 50 ml of acetonitrile, and 1.38 g of potassium carbonate (anydrous) was added thereto. The resultant mixture was stirred at room temperature for 2 hours, 2.14 g of β-bromoethyl-N-methylaniline was added, and the mixture heated for 3 hours under reflux. After cooling, crystals were filtered off. The filtrate was distilled under reduced pressure and the residue was purified by silica gel chromatography (eluent, benzene:ethyl acetate at 8:1) to give 3.82 g of the desired product, Compound 2, having nD24 1.5975 (yield 91.4%).

Workup

  1. temperaturethe mixture heated for 3 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationcrystals were filtered off
  5. distillationThe filtrate was distilled under reduced pressure
  6. customthe residue was purified by silica gel chromatography (eluent, benzene:ethyl acetate at 8:1)

Sources & evidence

ORD record
ord-113281265032450f84e2d9d5d0cacf69
Source dataset
uspto-grants-1984_07
Patent number
US04460597

Reaction notes

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