Sodium Chloride → N-(2,2-Dimethoxyethyl)-2-propenamide

HRID 1080753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1080753
[OH-].[Na+].[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH2:7].[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[Cl-].[Na+]>O.OC1CC(C)(C)[NH+]([O-])C(C)(C)C1>[CH3:3][O:4][CH:5]([O:8][CH3:9])[CH2:6][NH:7][C:10](=[O:13])[CH:11]=[CH2:12]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 13140Acryloyl chlorideHCID 14798Sodium Hydroxide2×HCID 89728Aminoacetaldehyde dimethyl acetal

Produkt 1

HCID 9898899N-(2,2-Dimethoxyethyl)-2-propenamideAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

40 g (1.0 mol) of sodium hydroxide are dissolved in 100 g of water and 200 g of ice in a 1-litre reactor having a stirrer and a cooling system. The sodium hydroxide solution is cooled to 10° C., and 105.1 g (1.0 mol) of aminoacetaldehyde dimethylacetal and 10 mg of the inhibitor 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxide are added. 99.5 g (1.1 mol) of acrylic acid chloride are slowly added to that solution at 10° C. over a period of 2 hours. The pH value drops slowly and ultimately is adjusted to 7. According to GC, amine is no longer present. The reaction mixture is saturated with sodium chloride and extracted three times with 200 ml of tert-butyl methyl ether. The organic phase is dried, filtered and concentrated using a rotary evaporator. The resulting oil is extracted three times with petroleum ether and then dried again using a rotary evaporator. 130 g of acrylamidoacetaldehyde dimethylacetal (81% of theory) are obtained in the form of an oil; the product is 99% according to GC.

Aufarbeitung

  1. extractionextracted three times with 200 ml of tert-butyl methyl ether
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. extractionThe resulting oil is extracted three times with petroleum ether
  7. customdried again
  8. customa rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-9a772c229cdd460e8d7bac12692311f5
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05583163

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