تفاعل #607435

معادلة التفاعل

(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

المردود 88.0%

المذيبات

DMF

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   غسيلsubsequently washed with H2O and brine
4. 4
   أخرىAter separation
5. 5
   تجفيفthe organic phase was dried over MgSO4
6. 6
   تركيزthen concentrated
7. 7
   أخرىThe residue was purified by chromatography on silica gel

الإجراء التجريبي

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).

المصدر