1H-1,2,4-Triazole → 4-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone

HRID 1085801Notes

Reaction equation

HRID 1085801 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10](Br)([CH3:12])[CH3:11])=[O:9])=[CH:4][CH:3]=1.[NH:14]1[CH:18]=[N:17][CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N:14]1([C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])([CH3:12])[CH3:11])[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 112999732-Bromo-1-(4-chlorophenyl)-2-methylpropan-1-one

Product 1

HCID 133668554-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketoneYield 25.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

80 g (0.31 mole) of 2-bromo-prop-2-yl 4-chlorophenyl ketone, 26.9 g (0.39 mole) of 1,2,4-triazole and 53.8 g (0.39 mole) of potassium carbonate are heated under reflux in 350 ml of acetone for 6 hours. The mixture is allowed to cool and is filtered and the filtrate 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 diisopropyl ether. 19.9 g (25.7% of theory) of 4-chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone of melting point 111° C. are obtained. ##STR19##

Workup

  1. temperatureto cool
  2. filtrationis filtered
  3. concentrationthe filtrate 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 diisopropyl ether

Sources & evidence

ORD record
ord-277a6eaca078433b9231c2c716a58751
Source dataset
uspto-grants-1991_04
Patent number
US05011850

Reaction notes

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