Reaction #607433

Reaction equation

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

potassium carbonate

N-methylhydroxylamine hydrochloride

2-propanol water

→

(2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-(3-methoxyphenyl)ethanimidamide

Yield 69.0%

Conditions

Workup

1. 1
   TemperatureThe reaction was heated
2. 2
   ExtractionThe residue was extracted with EtOAc
3. 3
   Washwashed with water
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated

Procedure

To a solution of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.00 g, 13.87 mmol, 1 eq.) in 2-propanol/water (60 ml/16 ml), was added potassium carbonate (3.84 g, 27.75 mmol, 2.0 eq) and N-methylhydroxylamine hydrochloride (2.32 g, 27.75 mmol, 2 eq.). The reaction was heated under stirring to 80° C. for 2 h. The residue was extracted with EtOAc and washed with water. The organics were combined, dried over MgSO4 and concentrated to give (2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-(3-methoxyphenyl)ethanimidamide (3.36, 69% yield), as a yellow solid.

Source