تفاعل #607432

معادلة التفاعل

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

المردود 91.0%

المذيبات

acetonitrile

DMF

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

الإجراء التجريبي

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.

المصدر