Reaktion #216703

Reaktionsgleichung

N-(Chlorocarbonyl)isocyanate

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

HCl

→

solid

Ausbeute 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

Ausbeute 64.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   TrocknenThe organic extracts were dried over MgSO4
3. 3
   SonstigeEvaporation and purification by flash chromatography on acid
4. 4
   Waschenwashed (5% H3PO4 /MeOH) silica gel (hexane/EtOAc 3/1)

Vorschrift

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

Quelle