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

HRID 1946615

반응식

HRID 1946615 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c7d5b70a48ac4dff9ba305b165af43f1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399452B2

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