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

HRID 2464

Reaction equation

HRID 2464 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.C(N(CC)CC)C>CS(C)=O>[CH:2]([CH2:3][N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=[O:1]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 19689855N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide

Product 1

HCID 19689822N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)benzamideYield 65.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

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.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-18e129f85987443abf273cc4ec32d571
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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