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 03/015519 for preparation) (95.4% purity, 15.85 g, 50.0 mmol) and 2-amino-5-cyano-N,3-dimethylbenzamide (i.e. the product of Example 6) (9.93 g, 52.5 mmol) in acetonitrile (120 mL) was added 3-picoline (17.5 mL, 16.7 g, 180 mmol). The mixture was cooled to −10° C., and then a solution of methanesulfonyl chloride (5.4 mL, 8.0 g, 70 mmol) was added dropwise at −10 to −5° C. The mixture was stirred for 5 minutes at this temperature, and then for 3 h at 0 to 5° C. Then water (55 mL) was added dropwise. The mixture was stirred for 15 minutes, then concentrated hydrochloric acid (5.0 mL, 60 mmol) was added dropwise and the mixture was stirred at 0 to 5° C. for 1 h. Then the mixture was filtered, and the solids were washed with 2:1 acetonitrile-water (2×10 mL), and then with acetonitrile (2×10 mL), and dried under nitrogen to afford the title compound as an off-white powder, 24.70 g (99.5% uncorrected yield), m.p. 177-181° C. (decomposition).

Provenance & Evidence