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Water → N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

HRID 1016578
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1016578
C([O:4][CH2:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[OH:4][CH2:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18407208N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline

Produkt 1

HCID 18407186N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyanilineAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In 6 ml of methanol was dissolved 525 mg of N-acetoxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline, and then 537 mg of potassium carbonate was added, followed by stirring at 50° C. for 7 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:3) and allowed to stand at room temperature to give 450 mg of N-hydroxyacetyl-N-(2-methoxybenzyl)-2-phenoxyaniline as crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% hydrochloric acid
  3. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:3)
  8. customto stand at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-2f824a14dcf8469fb49550af5c97bd34
Quelldatensatz
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06476056B2

Notizen zur Reaktion

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