Sulfuric Acid → 5-(2-Benzylaminopropoxy)salicylamide

HRID 615212

Reaktionsgleichung

Reaktionsgleichung von HRID 615212
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O=[C:15]([CH3:28])[CH2:16][O:17][C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1.[H][H]>CO.[Pt]>[CH2:1]([NH:8][CH:15]([CH3:28])[CH2:16][O:17][C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 7504BenzylamineHCID 137543335-(2-Oxopropoxy)salicylamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 137543345-(2-Benzylaminopropoxy)salicylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

55 g of benzylamine and 1.25 g of concentrated sulphuric acid are added to a solution of 104.5 g of 5-(2-oxopropoxy)salicylamide in 1000 ml of methanol and hydrogenated in the presence of 3.0 g of Pt/C-catalyst at room temperature and atmospheric pressure until 1 equivalent of hydrogen has been absorbed. The catalyst is filtered off, approximately 10 g of powdered calcium carbonate are stirred into the solution and the solution is filtered again and concentrated by evaporation. The oil remaining crystallises from isopropanol. Repeated recrystallisation from isopropanol yields 5-[2-(benzylamino)propoxy]salicylamide having a melting point of 102°-104°.

Aufarbeitung

  1. filtrationThe catalyst is filtered off
  2. filtrationthe solution is filtered again
  3. concentrationconcentrated by evaporation
  4. customThe oil remaining crystallises from isopropanol
  5. customrecrystallisation from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-63de6bddd2414f74b745644984c3ffc9
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497813

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