Diisopropylethylamine → 2-Methylthioethyl [1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinylpyrazol-5-yl]-N-methylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole (0.60 g, 1.3 mmol) and phosgene-toluene solution (20%, 0.85 g, 1.7 mmol) in tetrahydrofuran (8 ml) was added a solution of methylthioethanol (0.13 g, 1.46 mmol), diisopropylethylamine (0.51 g, 4.0 mmol) and 4-dimethylaminopyridine (0.05 g, 0.4 mmol) in tetrahydrofuran (10 ml) at 0-5° C. The mixture was stirred at 20° C. for 15 hours, then under reflux for 1 hour. Extractive workup (heptane-ethyl acetate, water) and chromatography gave the title product (Compound number 24-02, 0.57 g) as an oil; 1H-NMR: 2.08 (3H); 2.66 (2H); 3.10 (3H); 4.24 (2H); 7.80 (2H); 19F-NMR: −64.3; −72.7 (broad).

Provenance & Evidence