delta-Gluconolactone → Gluconamide

HRID 54897

Reaktionsgleichung

Reaktionsgleichung von HRID 54897
[C:1]1(=[O:12])[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].CCCCCCCCCCCCCC[N:27](CCC)CCC>CO>[O:12]=[C:1]([NH2:27])[C@@H:2]([C@H:4]([C@@H:6]([C@@H:8]([CH2:9][OH:10])[OH:11])[OH:7])[OH:5])[OH:3]

Komponenten

4

Edukt 2

HCID 7027delta-GluconolactoneHCID 110256N,N-dipropyltetradecan-1-amine

Produkt 1

HCID 124042GluconamideAusbeute 215,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A 1 liter round bottom flask equipped with a condenser, addition funnel, thermometer and mechanical stirrer was charged with D-glucono1,5-lactone (20.0 g, 0.11 mole) and methanol (56 g). The suspension was heated to 40° C. over 15 minutes and the heating mantle removed. Hydrogenated tallowaminopropylamine (36.0 g, 0.11 mole) was added dropwise over 15 minutes with rapid stirring. The reaction mixture was cooled and placed in a refrigerator at 0° C. overnight. The white product was filtered, washed with cold isopropanol (3×100ml) and dried under vacuum at 35° C. giving 46.2 g (83% yield) of hydrogenated tallowaminopropyl D-gluconamide with a melting point of 112°-115° C.

Aufarbeitung

  1. customA 1 liter round bottom flask equipped with a condenser, addition funnel
  2. customthe heating mantle removed
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe white product was filtered
  5. washwashed with cold isopropanol (3×100ml)
  6. customdried under vacuum at 35° C.

Quellen und Nachweise

ORD-Eintrag
ord-559569d379404b429437098030872744
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624906

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