Malononitrile → 1,1-Cyclohexanedicarbonitrile

HRID 12481

Reaction equation

HRID 12481 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 5445611,1-Cyclohexanedicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0f24ae48faae41c7bd08e7d80696285f
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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