Dimethylcarbamoyl Chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 748202

반응식

HRID 748202 반응식
[C:1]1([C:7]2[CH:12]=[CH:11][N+:10]([O-])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:18]#[N:19])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:18]([C:11]1[CH:12]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9][N:10]=1)#[N:19]

참가 물질

5

반응물 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 708034-Phenylpyridine-1-oxideHCID 82115Trimethylsilyl cyanide

생성물 1

HCID 877584-Phenyl-2-pyridinecarbonitrile수율 89%

시약·촉매·용매 1

HCID 6587Nitroethane용매

실험 절차

4-Phenylpyridine N-oxide (3.13 g, 18.3 mmol) was dissolved in nitroethane (30 ml), and trimethylsilyl cyanide (2.0 g, 20.2 mmol) and N,N-dimethylcarbamoyl chloride (1.7 ml, 18.5 mmol) were added thereto. The reaction mixture was stirred at room temperature for 45 hrs, concentrated under reduced pressure, combined with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The obtained crystals were collected by filtration, washed with diisopropyl ether and dried to give the titled compound (2.87 g, 89%). 1H-NMR (CDCl3) δ: 7.47-7.65 (5H, m), 7.72 (1H, dd, J=1.8, 5.2 Hz), 7.91 (1H, s), 8.75 (1H, d, J=5.1 Hz).

후처리

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationThe obtained crystals were collected by filtration
  7. washwashed with diisopropyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-2ec9959ab59a43ab848acc2abd8110f7
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399759B2

연결된 노트

불러오는 중…