2,2-Diethylmalononitrile → 1,3-Diamino-2,2-diethylpropane

HRID 12476

Reaktionsgleichung

Reaktionsgleichung von HRID 12476
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]([CH2:14][CH3:15])([C:12]#[N:13])[C:10]#[N:11])[CH3:8]>CCOCC>[CH2:7]([C:9]([CH2:14][CH3:15])([CH2:12][NH2:13])[CH2:10][NH2:11])[CH3:8]

Komponenten

4

Edukt 2

HCID 27772312,2-DiethylmalononitrileHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 4325891,3-Diamino-2,2-diethylpropane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A suspension of LiAlH4 (4.66 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of 2,2-diethyl-malononitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness under reduced pressure to give 5.0 g of a clear, light-yellow liquid. 1H NMR (400 MHz, CDCl3) δ 0.80 (t, J=8 Hz, 6H), 1.08 (br s, 4H), 1.22 (q, J=8 Hz, 4H), 2.52 (s, 4H).

Aufarbeitung

  1. temperaturewas cooled in an ice bath
  2. customwas kept below 20° C
  3. temperaturecooled in an ice bath
  4. customquenched
  5. additionby adding H2O (5 mL), 2M aqueous NaOH (10 mL) and again H2O (5 mL)
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with Et2O
  8. customthe combined filtrates were evaporated to dryness under reduced pressure
  9. customto give 5.0 g of a clear, light-yellow liquid

Quellen und Nachweise

ORD-Eintrag
ord-0f8d79ba1d9c4f4d8cc4deb72e397bf0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

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