Reacción #2560

ord-18e129f85987443abf273cc4ec32d571

Ecuación de reacción

COc1cccc(C(=O)N(CCO)c2ccccc2OC)c1
N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide
CCN(CC)CC
triethylamine
COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1
title compound
Rendimiento 65.6%
COc1cccc(C(=O)N(CC=O)c2ccccc2OC)c1
N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)benzamide
Rendimiento 65.6%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroat room temperature
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    Lavadowashed with water and saturated brine
  4. 4
    SecadoThe resulting organic layer was dried on anhydrous magnesium sulfate
  5. 5
    Otrothe solvent was removed by evaporation

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728835uspto-grants-1998_03