Reaction #2560

Reaction equation

N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide

triethylamine

→

title compound

Yield 65.6%

N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)benzamide

Yield 65.6%

Solvents

DMSO

DMSO

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Washwashed with water and saturated brine
4. 4
   DryingThe resulting organic layer was dried on anhydrous magnesium sulfate
5. 5
   Otherthe solvent was removed by evaporation

Procedure

In an atmosphere of argon, N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide (339 mg, 1.12 mmol) was dissolved in DMSO (4 ml) to which were subsequently added dropwise triethylamine (0.724 ml, 5.20 mmol) and a DMSO solution (8 ml) of a sulfur trioxide-pyridine complex (844 mg, 5.20 mmol) at room temperature. After 20 minutes of stirring at the same temperature, this was mixed with ice water (40 ml) and extracted with ethyl acetate, and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, and the solvent was removed by evaporation to obtain 220 mg (65.6%) of the title compound the form of light yellow solid.

Source