Hydrochloric Acid → Cyantraniliprole

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 2003/015519 for a method of preparation) (99.0% purity, 3.03 g, 0.01 mol) and 2-amino-5-cyano-N,3-dimethylbenzamide (prepared by the method of Example 2) (1.99 g, 0.01 mol) in acetonitrile (16 mL) was added 3-picoline (2.92 mL, 0.03 mol). Methanesulfonyl chloride (1.08 mL, 0.014 mol) was added dropwise to the reaction mixture at 20 to 25° C. After stirring for 3 h, water (7.5 mL) was added dropwise to the reaction mixture while maintaining the temperature between 20 to 25° C. After 15 minutes, concentrated hydrochloric acid (0.5 mL) was added and the reaction mixture was stirred for 1 h at 20 to 25° C. The mixture was filtered and the solids collected were washed with acetonitrile-water (87:13 mixture by volume, 2×2 mL) and then with water (2×2 mL), and then dried under nitrogen to afford the title compound (4.80 g, 92.6% corrected yield based on a water-free assay of 96.6%) as an off-white solid melting at 206-208° C.

Provenance & Evidence