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

HRID 2464

Reaktionsgleichung

Reaktionsgleichung von HRID 2464
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 19689822N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)benzamideAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-18e129f85987443abf273cc4ec32d571
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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