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

HRID 2755

反応式

HRID 2755 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 104996864-(Benzhydrylidene-amino)-3-bromomethyl-benzonitrile収率 56.9%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5d7a05761ee49b4bed0ffdf724b4bc7
出典データセット
uspto-grants-1998_03
特許番号
US05731315

関連ノート

読み込み中…