Reaction #607436

Reaction equation

(2Z)-2-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide

1,1′-carbonyldiimidazole

→

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

Yield 103.9%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherthe reaction was quenched by addition of water (100 ml)
2. 2
   Extractionextracted with EtOAc (2×100 ml)
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by chromatography on silica gel

Procedure

To a solution of (2Z)-2-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-phenylethanimidamide (1.8 g, 4.87 mmol, 1 eq.) in acetonitrile (120 ml), was added 1,1′-carbonyldiimidazole (1.58 g, 9.75 mmol, 2 eq.). After stirring at 80° C. for 1 hour, the reaction was quenched by addition of water (100 ml) and extracted with EtOAc (2×100 ml). The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (2 g, 100% yield).

Source