Benzoyl Peroxide → 4-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrile

HRID 2755

반응식

HRID 2755 반응식
[C:1](=[N:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH3:23])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1](=[N:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH2:23][Br:24])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 193509624-(Benzhydrylidene-amino)-3-methyl-benzonitrile

생성물 1

HCID 104996864-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrile수율 56.9%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-(benzhydrylidene-amino)-3-methyl-benzonitrile (1.36 g, 4.27 mmol) in 40 mL of CCl4 is added N-bromosuccinimide (0.84 g, 4.7 mmol) and benzoyl peroxide (0.22 g, 0.64 mmol). The solution is heated to reflux for 16 h. The solution is cooled to ambient temperatures. The solution is diluted with CH2Cl2. The solution is washed with 1N NaOH and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (0.91 g, 2.43 mmol) is obtained as an oil.

후처리

  1. temperatureThe solution is heated
  2. temperatureto reflux for 16 h
  3. temperatureThe solution is cooled to ambient temperatures
  4. washThe solution is washed with 1N NaOH and saturated NaCl
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material is purified by column chromatography
  9. washeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-d5d7a05761ee49b4bed0ffdf724b4bc7
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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