Réaction #9685

Équation de réaction

2-Amino-4-(trifluoromethyl)phenol

1-bromo-4-isothio-cyanatobenzene

→

title compound

Rendement 62.6%

N-(4-Bromophenyl)-5-(trifluoromethyl)-1,3-benzoxazol-2-amine

Rendement 62.6%

Solvants

ethyl alcohol

Conditions de réaction

Traitement

1. 1
   Températurebefore being heated
2. 2
   Températureat reflux overnight
3. 3
   Concentrationwas concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
5. 5
   Lavagewashed with 2 N aqueous hydrochloric acid solution and water
6. 6
   Séchagedried (Na2SO4)
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe residue was purified by flash chromatography on silica gel
9. 9
   Lavageeluting with 85:15 hexanes/ethyl acetate

Mode opératoire

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-ethylcarhodiimide 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.

Source