Dimethylcarbamoyl Chloride → 4-Phenyl-2-pyridinecarbonitrile

HRID 748202

反応式

HRID 748202 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 877584-Phenyl-2-pyridinecarbonitrile収率 89%

試薬・触媒・溶媒 1

HCID 6587Nitroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2ec9959ab59a43ab848acc2abd8110f7
出典データセット
uspto-grants-2008_07
特許番号
US07399759B2

関連ノート

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