Reacción #607432

Ecuación de reacción

potassium iodide

(2Z)-(hydroxyimino)(3-methoxyphenyl)acetonitrile

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

caesium carbonate

→

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

Rendimiento 91.0%

Disolventes

acetonitrile

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was then evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in EtOAc
3. 3
   Lavadosubsequently washed with H2O and brine
4. 4
   OtroAter separation
5. 5
   Secadothe organic phase was dried over MgSO4
6. 6
   Concentraciónthen concentrated

Procedimiento

To a solution of (2Z)-(hydroxyimino)(3-methoxyphenyl)acetonitrile (2.57 g, 14.59 mmol, 1 eq.) in 70 ml of acetonitrile and 7 ml of DMF, was added 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (2.87 g, 16.05 mmol, 1.1 eq.) followed by potassium iodide (242 mg, 1.46 mmol, 0.1 eq.) and caesium carbonate (10.45 g, 32.09 mmol, 2.2 eq.). The reaction was stirred 8 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 to afford (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.03 g, 91% yield, only 1 oxime isomer) which was used in the next step without further purification.

Fuente