반응 #607437

반응 방정식

potassium iodide

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

4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride

caesium carbonate

→

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

수율 80.0%

용매

acetonitrile

DMF

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 solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (7.3 g, 49.95 mmol, 1 eq.) in 280 ml of acetonitrile and 30 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (11.09 g, 59.94 mmol, 1.2 eq.) followed by potassium iodide (829 mg, 4.99 mmol, 0.1 eq.) and caesium carbonate (39.06 g, 119.88 mmol, 2.4 eq.). The reaction was stirred overnight 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-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (10.30 g, 80% yield, only 1 oxime isomer).

출처