1H-1,2,4-Triazole → 4-Fluoro-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one
Reaction equation
Br[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6].[NH:10]1[CH:14]=[N:13][CH:12]=[N:11]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:7][C:4]([CH3:8])([CH2:5][F:6])[C:3](=[O:9])[CH2:2][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1Participants
Procedure
197 g (1 mole) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone were slowly added dropwise to a boiling solution of 77 g (1.1 mols) of 1,2,4-triazole and 210 g (1.5 moles) of potassium carbonate in 500 ml of acetone such that, after removing the heating bath, the exothermic reaction kept the solution simmering. The mixture was then kept under reflux for a further 3 hours, the inorganic salts were filtered off and the filtrate was concentrated in vacuo. The residue was taken up in chloroform/water and the organic phase was separated off and evaporated. The residue which remained was distilled in vacuo and the distillate was crystallized with cyclohexane. 112 g (55% of theory) of 3,3-dimethyl-4-fluoro-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 59° C. were obtained. ##STR15##
Workup
- customafter removing the heating bath
- customthe exothermic reaction
- temperatureunder reflux for a further 3 hours
- filtrationthe inorganic salts were filtered off
- concentrationthe filtrate was concentrated in vacuo
- customthe organic phase was separated off
- customevaporated
- distillationThe residue which remained was distilled in vacuo
- customthe distillate was crystallized with cyclohexane
Sources & evidence
- ORD record
- ord-3f559018a0e2471697e58107e3058f3c
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04427672
Reaction notes
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