Benzophenone → 4-(Benzhydrylidene-amino)-3-methyl-benzonitrile

HRID 2754

反応式

HRID 2754 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:11](=[N:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 70103164-Amino-3-methylbenzonitrile

生成物 1

HCID 193509624-(Benzhydrylidene-amino)-3-methyl-benzonitrile収率 90.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-amino-3-methyl benzonitrile (1.20 g, 9.08 mmol) in 75 mL of toluene is added benzophenone (1.74 g, 9.53 mmol) and p-toluenesulfonic acid (0.43 g, 2.1 mmol). The reaction vessel is fitted with a Dean-Stark trap and the solution is heated at reflux. After 24 h, the solution is cooled to ambient temperatures. The solution is concentrated. The crude material is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (2.43 g, 8.2 mmol) is obtained as an oil.

後処理

  1. customThe reaction vessel is fitted with a Dean-Stark trap
  2. temperaturethe solution is heated
  3. temperatureat reflux
  4. temperaturethe solution is cooled to ambient temperatures
  5. concentrationThe solution is concentrated
  6. customThe crude material is purified by column chromatography
  7. washeluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-8506789e76894b63af6d91cbe4235510
出典データセット
uspto-grants-1998_03
特許番号
US05731315

関連ノート

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