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0 °C

A solution of aniline (18.4 mL, 202 mmol) in TEA (28.2 mL, 202 mmol) was added slowly to a cooled (0° C.) and stirred solution of 3,3-dichloro-1-[2,6-dichloro-4-(trifluoromethyl)-3-pyridinyl]-2-propen-1-one (22.9 g, 67.4 mmol) in dioxane (220 mL). The reaction was allowed to warm to room temperature and was stirred overnight. The mixture was treated with 10% HCI and extracted with Et2O (3×). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrate in vacuo. Silica gel flash chromatography of the residue using 6:1 Hex:EtOAc gave 3,3-dianilino-1-[2,6 dichloro-4-(trifluoromethyl)-3-pyridinyl]-2-propen-1-one as an off-white solid (13.10 g, 43%): 1H-NMR (d6-DMSO, 300 MHz) δ12.24 (br s, 1H), 9.20 (br s, 1H), 7.95 (s, 1H), 7.12-7.42 (m, 1H), 4.82 (s, 1H); Rf=0.60 (6:1 Hex:EtOAc).

1. temperatureto warm to room temperature
2. additionThe mixture was treated with 10% HCI
3. extractionextracted with Et2O (3×)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrate in vacuo