Water → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[methyl({[(1-phenylethylidene)amino]oxy}carbonyl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile

Participants

Reaction Steps

To a mixture of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole (0.5 g, 1.1 mmol), acetophenone-oxime (0.165 g, 1.2 mmol), diisopropylethylamine (0.43 g, 3.3 mmol) and 4-dimethylaminopyridine (41 mg, 0.3 mmol) in tetrahydrofuran (15 ml) was added a toluene solution of phosgene (0.66 g, 20%, 1.2 mmol) at 0-5° C. The mixture was stirred at reflux for 2 hours. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound 3-02, 0.14 g) as a solid; 1H-NMR: 2.25 (3H), 3.21 (3H), 7.42 and 7.68 (5H), 7.82 (2H); 19F-NMR: −64.3 (PhCF3); −72.9 (SO—CF3).

Provenance & Evidence