반응 #607435

반응 방정식

(2Z)-(hydroxyimino)(phenyl)acetonitrile

2-bromo-4-(bromomethyl)thiazole

potassium iodide

caesium carbonate

→

(2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile

수율 88.0%

용매

DMF

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   세척subsequently washed with H2O and brine
4. 4
   기타Ater separation
5. 5
   건조the organic phase was dried over MgSO4
6. 6
   농축then concentrated
7. 7
   기타The residue was purified by chromatography on silica gel

실험 절차

To a mixture of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.9 g, 19.84 mmol, 1 eq.), 2-bromo-4-(bromomethyl)thiazole (5.10 g, 19.84 mmol, 1 eq.), potassium iodide (329 mg, 1.98 mmol, 0.1 eq.) and caesium carbonate (9.70 g, 29.76 mmol, 1.5 eq.) was added 80 ml of acetonitrile and 10 ml of DMF. The reaction was stirred 2 h at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc, subsequently washed with H2O and brine. Ater separation, the organic phase was dried over MgSO4 then concentrated. The residue was purified by chromatography on silica gel to give (2Z)-{[(2-bromo-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (5.70 g, 88% yield, only 1 oxime isomer).

출처