تفاعل #607439

معادلة التفاعل

2-phenylethyl (4-{[({(1Z,2Z)-2-[ethyl(hydroxy)amino]-2-imino-1-phenylethylidene}amino)oxy]methyl}-1,3-thiazol-2-yl)carbamate

1,1′-carbonyldiimidazole

→

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

المردود 84.4%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was quenched by addition of water
2. 2
   استخلاصextracted with EtOAc
3. 3
   تجفيفdried over MgSO4
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by chromatography on silica gel

الإجراء التجريبي

To a solution of 2-phenylethyl (4-{[({(1Z,2Z)-2-[ethyl(hydroxy)amino]-2-imino-1-phenylethylidene}amino)oxy]methyl}-1,3-thiazol-2-yl)carbamate (160 mg, 71% purity, 0.24 mmol, 1 eq.) in acetonitrile (3 ml), was added 1,1′-carbonyldiimidazole (555 mg, 0.342 mmol, 1.4 eq.). After stirring at 80° C. for 6 hour, the reaction was quenched by addition of water and extracted with EtOAc. The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-ethyl-1,2,4-oxadiazol-5(2H)-one (70 mg, 55% yield).

المصدر