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

HRID 2754

Reaction equation

HRID 2754 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8506789e76894b63af6d91cbe4235510
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Linked notes

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