反应详情

温度

45 °C

1,2-Diamino-5-trifluoromethylbenzene (0.50 g, 2.84 mmol) was diluted in dichloromethane (5 mL) and treated with 4-bromo-2-fluoro-phenylisothiocyanate (0.66 g, 2.84 mmol). The dark solution was stirred at 45° C. for 15 minutes, then 1,3-dicyclohexylcarbodiimide (0.44 g, 2.13 mmol) was added all at once. The reaction was heated in a 45° C. oil bath overnight, then cooled and concentrated at reduced pressure. The dark residue was diluted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting dark brown oil was purified by flash chromatography on silica gel eluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate. The title compound was collected as a light pink solid (0.60 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ 11.3 (broad d, 1H), 9.87 (d, 1H), 7.50 (d, 2H), 7.61 (d, 1H), 7.55-7.41 (m, 3H), 7.35-7.30 (m, 1H); LC/MS m/z 356.2 (MH+), retention time 2.33 minutes.

1. temperatureThe reaction was heated in a 45° C. oil bath overnight
2. temperaturecooled
3. concentrationconcentrated at reduced pressure
4. additionThe dark residue was diluted with ethyl acetate
5. washthe organic layer was washed with water
6. dry with materialThe organic layer was dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe resulting dark brown oil was purified by flash chromatography on silica gel
9. washeluted on a gradient from 9:1 hexanes/ethyl acetate to 100% ethyl acetate
10. customThe title compound was collected as a light pink solid (0.60 g, 57%)