Triethylamine → 3-(Difluoromethyl)-N-methoxy-1-methyl-N-(1-methyl-2-(2,4,6-trichlorophenyl)ethyl)-1H-pyrazole-4-carboxamide

To a solution of O-Methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-hydroxylamine (0.65 g, 2.4 mmol) prepared as described in example P15d, in dichloromethane (5 ml) was added triethylamine (0.844 ml, 6.0 mmol) followed by drop wise addition of a solution 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride (0.519 g, 2.67 mmol) in dichloromethane at 0° C. After complete addition of acid chloride the mixture was stirred 18 hours at ambient temperature. When the TLC confirmed completion of the reaction, the reaction mass was diluted with water and extracted with dichloromethane (3×60 ml). The combined dichloromethane layer were washed with 2N HCl, followed by saturated NaHCO3, then with water and finally with brine solution before drying over sodium sulfate and evaporation of the solvent. The resulting crude mass was purified by column chromatography using 60-120μ mesh silica gel and product collected at 30% ethyl acetate in hexane as eluent to give 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1-methyl-2-(2,4,6-trichloro-phenyl)-ethyl]-amide (0.51 g, 49%) as off white solid. m.p: 110-112° C.

1. customcompletion of the reaction
2. extractionextracted with dichloromethane (3×60 ml)
3. washThe combined dichloromethane layer were washed with 2N HCl
4. dry with materialwith water and finally with brine solution before drying over sodium sulfate and evaporation of the solvent
5. customThe resulting crude mass was purified by column chromatography
6. customcollected at 30% ethyl acetate in hexane as eluent

ORD record

ord-500499bc962b46ed9679f64cb45bd270

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258169B2