1H-1,2,4-Triazole → 1-(4-Chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-one

HRID 1249148Notes

Reaction equation

HRID 1249148 reaction equation
Br[CH:2]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:3](=[O:12])[C:4]([CH3:11])([S:6][C:7]([F:10])([F:9])[F:8])[CH3:5].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1>C(#N)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH:2]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[C:3](=[O:12])[C:4]([CH3:11])([S:6][C:7]([F:10])([F:9])[F:8])[CH3:5])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 131173031-Bromo-1-(4-chlorophenoxy)-3-methyl-3-trifluoromethylthio-butan-2-one

Product 1

HCID 131173041-(4-Chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

29 g (0.075 mol) of crude 1-bromo-1-(4-chlorophenoxy)-3-methyl-3-trifluoromethylthio-butan-2-one and 16 g (0.25 mol) of 1,2,4-triazole in 150 ml of acetonitrile were heated under reflux for 1 hour. Thereafter, the mixture was concentrated and the residue was taken up with methylene chloride/water. The organic phase was separated off, dried over sodium sulphate and concentrated again. The oil residue was chromatographed. 10.4 g (37% of theory) of 1-(4-chlorophenoxy)-3-methyl-1-(1,2,4-triazol-1-yl)-3-trifluoromethylthio-butan-2-one of melting point 66° C. were obtained.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThereafter, the mixture was concentrated
  3. customThe organic phase was separated off
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated again
  6. customThe oil residue was chromatographed

Sources & evidence

ORD record
ord-258c49ee33d84da5a7ed1c23a456dcdb
Source dataset
uspto-grants-1986_12
Patent number
US04629732

Reaction notes

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