1H-1,2,4-Triazole → 4-(2,4-Dichlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butanone

HRID 329946Notes

Reaction equation

HRID 329946 reaction equation
Br[CH2:2][C:3](=[O:16])[C:4]([CH3:15])([CH3:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][C:7]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=1[CH2:5][C:4]([CH3:15])([CH3:14])[C:3](=[O:16])[CH2:2][N:17]1[CH:21]=[N:20][CH:19]=[N:18]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 133403811-Bromo-4-(2,4-dichlorophenyl)-3,3-dimethyl-2-butanone

Product 1

HCID 133403824-(2,4-Dichlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butanoneYield 45.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

30 g (0.09 mole) of 1-bromo-4-(2,4-dichlorophenyl)-3,3-dimethyl-2-butanone, 12.4 g (0.18 mole) of 1,2,4-triazole and 24.8 g (0.18 mole) of potassium carbonate are heated under reflux in 300 ml of acetone for 6 hours. The mixture is then allowed to cool and is filtered with suction and the mother liquor is concentrated in vacuo. The residue is taken up in methylene chloride and the mixture is washed with water, dried over sodium sulphate and concentrated in vacuo. The residue is recrystallised from diethyl ether. 12.8 g (45.6% of theory) of 4-(2,4-dichlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone of melting point 85° C. are obtained. ##STR14##

Workup

  1. temperatureto cool
  2. filtrationis filtered with suction
  3. concentrationthe mother liquor is concentrated in vacuo
  4. washthe mixture is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallised from diethyl ether

Sources & evidence

ORD record
ord-e73acc9589344cf3af29f60ce5376547
Source dataset
uspto-grants-1990_01
Patent number
US04894382

Reaction notes

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