Reaction #607428

Reaction equation

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

Yield 80.0%

Solvents

acetonitrile

DMF

Conditions

Workup

1. 1
   OtherThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   Washsubsequently washed with H2O and brine
4. 4
   OtherAter separation
5. 5
   Dryingthe organic phase was dried over MgSO4
6. 6
   Concentrationthen concentrated
7. 7
   OtherThe residue was purified by chromatography on silica gel

Procedure

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).

Source