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

HRID 2754

반응식

HRID 2754 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 193509624-(Benzhydrylidene-amino)-3-methyl-benzonitrile수율 90.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8506789e76894b63af6d91cbe4235510
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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