Malononitrile → 1,1-Cyclohexanedicarbonitrile

HRID 1024342

반응식

HRID 1024342 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 5445611,1-Cyclohexanedicarbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6fd184aa2b2d410cbf5673a32407f20a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722887B2

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