반응 #2294043

반응 방정식

N′-hydroxy-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide

iodomethylcyclopropane

cesium carbonate

Iodomethylcyclopropane

cesium carbonate

potassium iodide

→

N′-(cyclopropylmethoxy)-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide

수율 11.7%

용매

Water

DMF

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   건조dried over MgSO4
3. 3
   기타evaporated
4. 4
   기타The residue was purified by chromatography on silica gel

실험 절차

A solution of N′-hydroxy-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide (150 mg, 0.392 mmol, 1 eq), iodomethylcyclopropane (0.069 ml, 0.588 mmol, 1.5 eq) and cesium carbonate (191 mg, 0.588 mmol, 1.5 eq) in DMF (3 ml) was stirred at 80° C. for 7 h and overnight at room temperature. Iodomethylcyclopropane (0.069 ml, 0.588 mmol, 1.5 eq), cesium carbonate (191 mg, 0.588 mmol, 1.5 eq) and potassium iodide (0.1 eq) were then added and the mixture was stirred at 60° C. for 8 h. Water was added and the mixture was extracted with ethyl acetate. The organics were combined, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica gel to afford N′-(cyclopropylmethoxy)-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide (20 mg, 10% yield) as a transparent oil.

출처