反应详情

2-Amino-4-(trifluoromethyl)phenol (250 mg, 1.41 mmol) and 1-bromo-4-isothio-cyanatobenzene (302 mg, 1.41 mmol) were stirred in ethyl alcohol at ambient temperature for 18 h. The flask was charged with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (405 mg, 2.12 mmol), and the mixture was stirred for 2 h before being heated at reflux overnight. The reaction was allowed to cool to rt and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 2 N aqueous hydrochloric acid solution and water, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 85:15 hexanes/ethyl acetate to provide the title compound (315 mg, 62%). LC-MS m/z 357.1 (MH+), retention time 4.20 minutes.

1. temperaturebefore being heated
2. temperatureat reflux overnight
3. concentrationwas concentrated under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate
5. washwashed with 2 N aqueous hydrochloric acid solution and water
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography on silica gel
9. washeluting with 85:15 hexanes/ethyl acetate