Lactonitrile → 2-(Diisopropylamino)propionitrile

HRID 374667

Reaktionsgleichung

Reaktionsgleichung von HRID 374667
S([O-])([O-])(=O)=O.[Mg+2].[CH:7]([NH:10][CH:11]([CH3:13])[CH3:12])([CH3:9])[CH3:8].[C:14](#[N:18])[CH:15]([CH3:17])O>C(OCC)C>[CH:7]([N:10]([CH:11]([CH3:13])[CH3:12])[CH:15]([CH3:17])[C:14]#[N:18])([CH3:9])[CH3:8]

Komponenten

5

Edukt 3

HCID 6572LactonitrileHCID 7912DiisopropylamineHCID 24083Sulfuric acid magnesium salt (1:1)

Produkt 1

HCID 109972602-(Diisopropylamino)propionitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
51 °C

Versuchsvorschrift

Anhydrous magnesium sulfate (12.04 g, 0.1 mol) was added to diisopropylamine (12.14 g, 0.12 mol), followed by lactonitrile (7.73 g of 92% aqueous solution, 0.1 mol) added all at once with stirring. The reaction mixture spontaneously warmed up to 51° C. It was left overnight at room temperature. Diethyl ether (50 ml) was added, and magnesium sulfate was filtered off and washed with ether (50 ml). The product was isolated by distillation, 11.57 g, 75% yield, bp 49°-50° C./0.1 mm Hg. 1H NMR CDCl3 δ ppm, 1.02 (d, J=6.5 Hz, 6H, CH3), 1.17 (d, J=6.5 Hz, 6H, CH3), 1.41 (d, J=6.5 Hz, 3H, CH3, 3.21 (sep, J=6.5 Hz, 2H,=CH) , 3.89 (q, J=6.5 Hz, 1H, CH) .

Aufarbeitung

  1. additionadded all at once
  2. filtrationmagnesium sulfate was filtered off
  3. washwashed with ether (50 ml)
  4. customThe product was isolated by distillation, 11.57 g, 75% yield, bp 49°-50° C./0.1 mm Hg

Quellen und Nachweise

ORD-Eintrag
ord-c47826333e954a139ba74d6485ed7449
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05481038

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