p-Toluenesulfonic acid → Benzonitrile, 4-[[(4-propylphenyl)methylene]amino]-

HRID 1439145Notes

Reaction equation

HRID 1439145 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)[CH2:11][CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 1200474-Propylbenzaldehyde

Product 1

HCID 170100Benzonitrile, 4-[[(4-propylphenyl)methylene]amino]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.9 g. of p-aminobenzonitrile and 7.4 g. of p-n-propylbenzaldehyde in 100 ml. of benzene is treated with 150 mg. of p-toluenesulfonic acid and reacted as described in Example 1. After evaporation, there remain 12.5 g. of a yellowish oil which crystallizes with cooling. Purification is carried out by several recrystallizations from isopropanol as described in Example 1. The p-[(p-n-propylbenzyliden)amino]-benzonitrile which is obtained has a melting point of 64.8°-65.5° C. and a clearing point of 77.6° C. UV (ethanol): ε280 = 24300 (shoulder at 310 nm). The nuclear magnetic resonance, mass spectrum, infrared and microanalysis data confirm the structure.

Workup

  1. additionA mixture of 5.9 g
  2. customAfter evaporation, there
  3. customof a yellowish oil which crystallizes
  4. temperaturewith cooling
  5. customPurification
  6. customis carried out by several recrystallizations from isopropanol

Sources & evidence

ORD record
ord-cca372e8ccf049278930af7cc068a889
Source dataset
uspto-grants-1977_11
Patent number
US04058477

Reaction notes

Loading…