Reaction #607432

Reaction equation

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

Yield 91.0%

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

Procedure

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.

Source