Реакция #607434

Уравнение реакции

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

Выход 77.0%

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture was refluxed for 15 h
2. 2
   КонцентрированиеAfter concentration
3. 3
   Другоеthe residue was purified by chromatography on silica gel

Методика

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.

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