Dibenz(b,f)azepine → (Z)-2-(5H-dibenzo[b,f]azepin-5-yl)acetonitrile

HRID 1946615

反応式

HRID 1946615 の反応式
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S([O-])([O-])(=O)=O.[CH2:21]([N+:25](CCCC)(CCCC)CCCC)[CH2:22]CC.C([N+](CCCC)(CCCC)CCCC)CCC.BrCC#N.[OH-].[Na+]>C(Cl)Cl.O>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:22][C:21]#[N:25])[C:5]=2[CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 9212Dibenz(b,f)azepineHCID 11534BromoacetonitrileHCID 14798Sodium HydroxideHCID 11433187Bis(tetrabutylammonium) sulphate

生成物 1

HCID 11345294(Z)-2-(5H-dibenzo[b,f]azepin-5-yl)acetonitrile収率 51.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

(Z)-5H-dibenzo[b,f]azepine (0.1 g, 0.5 mmol), tetrabutylammonium sulfate (0.35 g, 1.0 mmol), 2-bromoacetonitrile (0.4 mL, 5.0 mmol) and 50% aqueous sodium hydroxide (1 mL) were mixed in DCM (1 mL) and the reaction mixture was stirred for 5 days. The mixture was diluted in water and the aqueous layer was extracted with DCM (2 times). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0% to 50% ethyl acetate in hexanes) to afford title compound 365 (60 mg, 50%). 1H NMR (CDCl3) δ (ppm): 7.36-7.31 (m, 2H), 7.26-7.23 (m, 2H), 7.17-7.11 (m, 4H), 6.76 (s, 2H), 4.47 (s, 2H).

後処理

  1. extractionthe aqueous layer was extracted with DCM (2 times)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (0% to 50% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c7d5b70a48ac4dff9ba305b165af43f1
出典データセット
uspto-grants-2013_03
特許番号
US08399452B2

関連ノート

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