1H-1,2,4-Triazole → 3-Methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylmercaptobutan-2-one

HRID 464921Notes

Reaction equation

HRID 464921 reaction equation
Br[CH2:2][C:3](=[O:12])[C:4]([CH3:11])([S:6][C:7]([F:10])([F:9])[F:8])[CH3:5].[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:5][C:4]([S:6][C:7]([F:10])([F:9])[F:8])([CH3:11])[C:3](=[O:12])[CH2:2][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 131173011-Bromo-3-methyl-3-trifluoromethylthio-butan-2-one

Product 1

HCID 130735653-Methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylmercaptobutan-2-oneYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

26.5 g (0.1 mol) of 1-bromo-3-methyl-3-trifluoromethylthio-butan-2-one were added dropwise to a mixture of 8.3 g (0.12 mol) of 1,2,4-triazole and 28 g (0.2 mol) of potassium carbonate in 150 ml of acetone at room temperature. The mixture was subsequently stirred under reflux for 1 hour, the inorganic salts were filtered off and the filtrate was concentrated. The residue was taken up in methylene chloride, washed with water, dried over sodium sulphate and distilled. 15.5 g (62% of theory) of 3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylmercapto-butan-2-one of boiling point 91° C./0.5 mm Hg and of melting point ~45° C. were obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. filtrationthe inorganic salts were filtered off
  3. concentrationthe filtrate was concentrated
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled

Sources & evidence

ORD record
ord-9e875f8a3cd04bd0bef107e70566c124
Source dataset
uspto-grants-1985_10
Patent number
US04549900

Reaction notes

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