2,2-Diethoxyethylamine → alpha-(2,2-Diethoxyethylamino)-beta-nitrostyrene

HRID 1033567

Reaktionsgleichung

Reaktionsgleichung von HRID 1033567
[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O)([O-:3])=[O:2].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH2:18])[CH3:14]>C1(C)C=CC=CC=1>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][NH:18][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH:4][N+:1]([O-:3])=[O:2])[CH3:14]

Komponenten

4

Edukt 2

HCID 695242,2-DiethoxyethylamineHCID 948332-Nitro-1-phenylethanone

Produkt 1

HCID 67799143alpha-(2,2-Diethoxyethylamino)-beta-nitrostyreneAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Alpha-nitro acetophenone (5.7 g, 0.0345 mol) is taken up in 100 mL toluene and 4.6 g (0.0345 mol) of amino acetaldehyde diethyl acetal is added. The reactants are put into a 250 mL RB flask fitted with a Dean-Stark trap. The trap is filled with 4A molecular sieves and the mixture is heated at reflux for 18 hours. The toluene is removed in vacuo to give 8.36 g of α-(2,2-diethoxyethylamino)-β-nitrostyrene as a brown oil. To this oil is added 50 mL of concentrated HCl. As the flask is swirled the oil turns to a yellow suspension. After 10 minutes the solid is filtered to give 2.48 g of a yellow solid. Recrystallization from ether/ethylacetate/hexane gives the product as two fractions, 2.08 g of mp 190°-192° C.

Aufarbeitung

  1. customThe reactants are put into a 250 mL RB flask
  2. customfitted with a Dean-Stark trap
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 18 hours
  5. customThe toluene is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f4ffeebef524227a5720f49c2c383fd
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310938

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