Benzophenone imine → 2-(Benzhydrylideneamino)-4-methylbenzonitrile

HRID 1432856Notes

Reaction equation

HRID 1432856 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11](=N)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClC(Cl)C>[C:11](=[N:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 179851672-(Benzhydrylideneamino)-4-methylbenzonitrileYield 78.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-amino-4-methyl benzonitrile (20 g, 151 mmol) in 1000 mL of dichloroethane is added benzophenone imine (30 g, 166 mmol). The solution is refluxed for 48 hours After this time, the solution is cooled to ambient temperatures. The solution is washed with sat. NaHCO3, water and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated under vacuum. The product is further purified by recrystallization from t-butyl ether. The title compound (25.5 g, 118 mmol) is obtained as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ7.88 (m, 2H), 7.42 (m, 3H), 7.32 (m, 7H), 6.79 (d, 1H), 6.58 (s, 1H), 2.23 (s, 3H).

Workup

  1. temperatureThe solution is refluxed for 48 hours After this time
  2. temperaturethe solution is cooled to ambient temperatures
  3. washThe solution is washed with sat. NaHCO3, water and sat. NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe product is further purified by recrystallization from t-butyl ether

Sources & evidence

ORD record
ord-a98c07e4249b4360b2610b775e6724fb
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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