Thionyl Chloride → 2-Chloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-cyano-6-fluorobenzimidoyl chloride

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Reaction Steps

A solution of 2-chloro-N-(2-chloro-3-fluoro-pyridin-4-yl)-4-cyano-6-fluorobenzamide (0.805 g, 2.5 mmol) in thionyl chloride (7.5 mL) was heated under reflux for 65 h then cooled to ambient temperature. The reaction mixture was diluted with toluene and concentrated under reduced pressure to give the desired compound as a yellow solid (0.814 g, 96% yield). 1H NMR (300 MHz, CDCl3): δ 8.25 (d, J=5.1 Hz, 1H), 7.70-7.63 (m, 1H), 7.49 (dd, J=8.0, 1.0 Hz, 1H), 6.97 (t, J=5.0 Hz, 1H). LCMS (Method D): RT=4.09 min, m/z: 346 [M+H+].

Provenance & Evidence