Реакция #216703

Уравнение реакции

N-(Chlorocarbonyl)isocyanate

(E)-N-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-hydroxylamine

HCl

→

solid

Выход 64.0%

(E)-2-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-[1,2,4]oxadiazolidine-3,5-dione

Выход 64.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with EtOAc
2. 2
   СушкаThe organic extracts were dried over MgSO4
3. 3
   ДругоеEvaporation and purification by flash chromatography on acid
4. 4
   Промывкаwashed (5% H3PO4 /MeOH) silica gel (hexane/EtOAc 3/1)

Методика

N-(Chlorocarbonyl)isocyanate (0.37 ml, 4.63 mmol) was added dropwise to a cold (-5° C.) mixture of (E)-N-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-hydroxylamine (2.0 g, 4.63 mmol) in THF (20 ml). The mixture was stirred for 30 minutes, then poured into HCl (1N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acid washed (5% H3PO4 /MeOH) silica gel (hexane/EtOAc 3/1) gave a white solid (1.48 g, 64% yield, mp 66°-67° C.). Analysis for: C25H22F3N3O5Calc'd: C, 59.88; H, 4.42; N, 8.38 Found: C, 59.83; H, 4.37; N, 8.28

Источник