Реакция #75939

Уравнение реакции

HCl

N-(Chlorocarbonyl)isocyanate

N-{4′-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine

tetrahydrofuran

→

solid

Выход 53.0%

2-{4′-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-[1,2,4]oxadiazolidine-3,5-dione

Выход 53.0%

Растворители

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate
2. 2
   СушкаThe organic extracts were dried over MgSO4
3. 3
   ДругоеEvaporation and purification by flash chromatography on acidic silica gel (hexanes/EtOAc 2:1)

Методика

N-(Chlorocarbonyl)isocyanate (0.2 mL, 2.6 mmol) was added dropwise into a cold (−5° C.) mixture of N-{4′-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine (1.1, 2.6 mmol), and tetrahydrofuran (20.0 mL). The reaction mixture was stirred for 30 minutes, poured into water, acidified with HCl (2 N), and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acidic silica gel (hexanes/EtOAc 2:1) gave a white solid (0.68 g, 53% yield): mp 196-198; MS m/e 493 (M+);

Источник