HCID 23362032, Verbindung → HCID 68762744, Verbindung

HRID 1398935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1398935
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](N)[C:3]=1[NH:9][CH2:10][CH2:11][OH:12].Cl.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([OH:27])[C:23](=[NH:26])OC>C(O)C.C(=O)([O-])O.[Na+]>[NH2:1][C:2]1[C:3]2[N:9]([CH2:10][CH2:11][OH:12])[C:23]([CH:22]([C:16]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=3[Cl:14])[OH:27])=[N:26][C:4]=2[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 23362032HCID 23362032, VerbindungHCID 68736952HCID 68736952, Verbindung

Produkt 1

HCID 68762744HCID 68762744, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[(2,6-diaminophenyl)amino]ethanol (3.63 g, 21.7 mmol) in ethanol (43 mL) was added methyl 2-(2,4-dichlorophenyl)-2-hydroxyethanimidoate hydrochloride (7.04 g, 26.0 mmol) at room temperature. After 12 h, the reaction mixture was diluted with aqueous sodium hydrogen carbonate. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate to give the title compound as an orange amorphous solid (7.58 g, 21.5 mmol, 99%).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3f6a9aa63cfe46e6b8c1cff0419962e0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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