p-Toluidine → N-(p-phenylbenzylidene)-p-methylaniline

HRID 261829Notes

Reaction equation

HRID 261829 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:17]1([C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[N:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=3)=[CH:13][CH:14]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 76689(1,1'-Biphenyl)-4-carboxaldehyde

Product 1

HCID 13017554N-(p-phenylbenzylidene)-p-methylaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-toluidine (0.20 mole), 4-biphenylaldehyde (0.20 mole), and IRC-50 (weakly acidic) ion exchange resin (0.5 g.) are azeotropically refluxed in toluene (150 cc). The required amount of water is removed after about 3 hours. The solvent is removed on the rotary, and the residue is recrystallized with 95% ethanol to yield N-[(p-phenyl)benzylidene]-p-methylaniline. m.p. 137°-139° C.

Workup

  1. customThe required amount of water is removed after about 3 hours
  2. customThe solvent is removed on the rotary, and the residue
  3. customis recrystallized with 95% ethanol

Sources & evidence

ORD record
ord-a900ef8de75a40729911d326bbceac00
Source dataset
uspto-grants-1979_05
Patent number
US04152452

Reaction notes

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