Реакция #607431

Уравнение реакции

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

pyridine

4-chlorophenyl acetyl chloride

→

2-(4-chlorophenyl)-N-{4-[({[(Z)-(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}acetamide

Выход 83.3%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched by addition of 2 ml of 1N NaOH
2. 2
   ДругоеThe layers were separated
3. 3
   Сушкаthe organic layer was dried over MgSO4
4. 4
   КонцентрированиеAfter concentration
5. 5
   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 (300 mg, 0.905 mmol, 1 eq.) and pyridine (0.110 ml, 1.36 mmol, 1.5 eq) in dry dichloromethane (4.0 ml) at room temperature was added 4-chlorophenyl acetyl chloride (0.20 mL, 1.36 mmol, 1.5 eq) and stirring was allowed for 2 h. The reaction was quenched by addition of 2 ml of 1N NaOH. The layers were separated and the organic layer was dried over MgSO4. After concentration, the residue was purified by chromatography on silica gel to give 2-(4-chlorophenyl)-N-{4-[({[(Z)-(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}acetamide (365 mg, 79% yield).

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