Dimethylformamide → 5-(4-acetoxymethyl-3-chlorophenyl)-3-(2-chloro-6-fluorophenyl) 1-methyl-1H-1,2,4-triazole

HRID 52243

Reaction equation

CN(C)C=O.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:27])[N:15]=2)=[CH:10][C:9]=1[Cl:28].[C:29]([O-:32])(=[O:31])[CH3:30].[K+]>O>[C:29]([O:32][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]([CH3:19])[N:17]=[C:16]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:27])[N:15]=2)=[CH:10][C:9]=1[Cl:28])(=[O:31])[CH3:30]

Participants

Conditions

Temperature: 130 °C

Procedure

To N,N-dimethylformamide (200 ml) are added 5-(4-bromomethyl-3-chlorophenyl)-3(2-chloro-6-fluorophenyl)-1-methyl-1H-1,2,4-triazole (24.3 g) and potassium acetate (29.0 g), which are stirred at 130° C. for 3 hours. The reaction mixture is cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate is purified by silica gel column chromatography using mixed solvent of hexaneethyl acetate as eluent to give 11.8 g of desired compound.

Workup

temperatureThe reaction mixture is cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer is washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe concentrate is purified by silica gel column chromatography
additionusing mixed solvent of hexaneethyl acetate as eluent

Sources & evidence

ORD record: ord-8fa665d60d0042bb9c1b74ac3290d927
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616594

Linked notes

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