Dimethylformamide → HCID 86709874, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4,5-dichloro-6-(4-chlorophenyl)picolinic acid (3.00 g, 9.9 mmol) in toluene (25 mL) was added thionyl chloride (1.08 mL, 14.9 mmol) and dimethylformamide (0.04 mL, 0.5 mmol). Reaction mixture was heated at 80° C. for 2.5 h. HPLC analysis of the reaction mixture treated with methanol and dimethylaminopyridine indicated starting material remaining. Reaction mixture was allowed to cool to room temperature and additional thionyl chloride (0.5 mL, 6.9 mmol) and dimethylformamide (0.04 mL, 0.5 mmol) were added. Reaction was heated at 80° C. for an additional 2 h. Reaction was allowed to cool to room temperature and concentrated under reduced pressure to provide a white solid. Toluene (40 mL) was added to dissolve the solid and concentrated under reduced pressure and then this process was performed a second time. 4,5-Dichloro-6-(4-chlorophenyl)picolinoyl chloride was isolated as a white solid (3.05 g, 96% yield). 1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.79-7.72 (m, 2H), 7.53-7.46 (m, 2H). 13C NMR (101 MHz, CDCl3) δ 168.66, 157.63, 146.48, 145.44, 136.35, 135.10, 134.28, 131.04, 128.63, 124.90. LRMS: Calcd. for C12H5Cl4NO, 320.91. Found: m/z=257 (M+-COCl), 222, 207, 186, 151.

Provenance & Evidence