Malononitrile → 1,1-Cyclohexanedicarbonitrile

HRID 12481

Reaktionsgleichung

Reaktionsgleichung von HRID 12481
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6]1[CH2:16][CH2:15]N2C(=NCCC2)[CH2:8][CH2:7]1.BrCCCCCBr>CN(C=O)C>[C:2]1([C:1]#[N:5])([C:3]#[N:4])[CH2:15][CH2:16][CH2:6][CH2:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 8010MalononitrileHCID 81001,5-DibromopentaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 5445611,1-Cyclohexanedicarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Malononitril (15.0 g) was dissolved in dry DMF (200 mL). Subsequently, DBU (75 mL) and 1,5-dibromopentane (34 mL) were added at 0° C. (ice bath). The ice bath was removed and the reaction was stirred for 2 h at 80° C. After cooling down, the reaction was poured into DCM. The organic layer was washed several times with 5% NaHCO3, the organic layer dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography eluting with PA:EtOAc (9:1) yielding 25.7 g white crystals. 1H NMR (400 MHz, CDCl3) δ 1.48-1.61 (m, 2H), 1.68-1.84 (m, 4H), 2.13 (t, J=6 Hz, 4H).

Aufarbeitung

  1. customThe ice bath was removed
  2. temperatureAfter cooling down
  3. additionthe reaction was poured into DCM
  4. washThe organic layer was washed several times with 5% NaHCO3
  5. dry with materialthe organic layer dried over Na2SO4
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography
  8. washeluting with PA

Quellen und Nachweise

ORD-Eintrag
ord-0f24ae48faae41c7bd08e7d80696285f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

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