Water → 5-(2-chloro-6-fluorophenyl)-3-(4-chloro-alpha,alpha-dimethylbenzyl)-1-methyl-1H-1,2,4-triazole
Reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([CH3:7])[C:3](Cl)=[N:4][NH2:5].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:17]=1[C:18]#[N:19].[Cl-].[Al+3].[Cl-].[Cl-].O.Cl[C:31]1C=CC=CC=1Cl>>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:17]=1[C:18]1[N:5]([CH3:31])[N:4]=[C:3]([C:2]([CH3:7])([CH3:1])[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:19]=1Participants
6
Reactant 5
Product 1
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 0.7 g of N-methyl-N-(p-toluenesulfonyl)-(α, α-dimethyl-4-chlorophenylacetohydrazonoyl chloride in 7 ml of o-dichlorobenzene at room temperature, were added 0.33 g of 2-chloro-6-fluorobenzonitrile and 0.28 g of anhydrous aluminium chloride, and the reaction mixture was heated at 120° C. for 30 minutes. After cooling, the reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.6 g of 5-(2-chloro-6-fluorophenyl)-3-(4-chloro-α,α-dimethylbenzyl)-1-methyl-1H-1,2,4-triazole. m.p.97°-100° C.
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d78e0ccdc1964e0599130b92559e95f0
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05892048
Reaction notes
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