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Isatoic Anhydride → 2-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

HRID 1608817
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1608817
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[NH2:13][CH2:14][CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1>C(O)(C)C.C(OCC)(=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:13][CH2:14][CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 8359Isatoic AnhydrideHCID 30821451H-Imidazole-2-ethanamine

Produkt 1

HCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamideAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Twenty grams (0.123 mol) of isatoic anhydride were slowly added to a cold (0° C.) solution of 13.5 g (0.122 mol) of 2-(2-aminoethyl)imidazole in 220 ml isopropanol, under nitrogen. The reaction mixture was gradually warmed to room temperature and allowed to react. When the reaction was complete, as indicated by thin layer chromatography, the solution was reduced to dryness under reduced pressure and the resultant residue was redissolved in an ethyl acetate/aqueous sodium bicarbonate mixture. The resulting layers were separated, the organic layer was washed with water and reduced to dryness to provide a solid. This solid was recrystallized from ethanol containing a small amount of hexane to provide 24.1 g of the desired subtitled intermediate (m.p. 180°-185° C.).

Aufarbeitung

  1. customto react
  2. customThe resulting layers were separated
  3. washthe organic layer was washed with water
  4. customto provide a solid
  5. customThis solid was recrystallized from ethanol containing a small amount of hexane

Quellen und Nachweise

ORD-Eintrag
ord-80fb02e441474e73a92b956199ece31f
Quelldatensatz
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05397798

Notizen zur Reaktion

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