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Sodium Bicarbonate → N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamide

HRID 2463
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2463
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[C:6]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[CH2:9][CH2:10][O:11]C1CCCCO1)=[O:7].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[OH:11][CH2:10][CH2:9][N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:24][CH3:25])[C:6](=[O:7])[C:5]1[CH:26]=[CH:27][CH:28]=[C:3]([O:2][CH3:1])[CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 539260843-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide

Produkt 1

HCID 19689855N-(2-hydroxyethyl)-3-methoxy-N-(2-methoxyphenyl)benzamideAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

3-Methoxy-N-(2-methoxyphenyl)-N-(2-tetrahydropyranyloxyethyl)benzamide (501 mg, 1.30 mmol) was dissolved in methanol (4 ml) to which was subsequently added a catalytically effective amount of p-toluenesulfonic acid monohydrate and stirred for 3 hours at room temperature. The reaction solution was mixed with saturated sodium bicarbonate aqueous solution (10 ml) and extracted with ether, and then washed with water and saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting colorless oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:1) to obtain 340 mg (86.8%) of the title compound in the form of light yellow oil.

Aufarbeitung

  1. extractionextracted with ether
  2. washwashed with water and saturated brine
  3. dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customthe resulting colorless oily residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-cbf5b75d0c184a8f8de856d128b7a42f
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728835

Notizen zur Reaktion

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