反応 #607434

反応方程式

Cyclohexanol

pyridine

3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one

acetonitrile

→

Cyclohexyl {4-[({[(Z)-(3-methoxyphenyl)(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate

収率 77.0%

反応条件

後処理

1. 1
   温度the resulting mixture was refluxed for 15 h
2. 2
   濃縮After concentration
3. 3
   その他the residue was purified by chromatography on silica gel

実験手順

To a solution of 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (100 mg, 0.277 mmol, 1 eq.) in acetonitrile (2 ml) was added 4-fluorophenylcarbonochloridate (0.040 mL, 0.304 mmol, 1.1 eq.), followed by pyridine (0.022 mL, 0.277 mmol, 1 eq.) and stirring was allowed for 2 hours at room temperature. Cyclohexanol (0.032 mL, 0.304 mmol, 1.1 eq.) was then added and the resulting mixture was refluxed for 15 h. After concentration, the residue was purified by chromatography on silica gel to give Cyclohexyl {4-[({[(Z)-(3-methoxyphenyl)(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate (110 mg, 77% yield) as a white solid.

出典