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

HRID 1658162Notes

Reaction equation

HRID 1658162 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:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13][CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 23290Benzaldehyde, 4-pentyl-

Product 1

HCID 170810Benzonitrile, 4-[[(4-pentylphenyl)methylene]amino]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.9 g. of p-aminobenzonitrile and 8.8 g. of p-n-pentylbenzaldehyde 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 13.9 g. of a yellow oil which crystallizes with cooling. Purification is carried out by several recrystallizations from isopropanol as described in Example 1. The p-[(p-n-pentylbenzyliden)amino]benzonitrile which is obtained has a melting point of 45.6°-46.4°C. and a clearing point of 75.0°C. UV (ethanol): ε279 = 24400 (shoulder at 314 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 yellow oil which crystallizes
  4. temperaturewith cooling
  5. customPurification
  6. customis carried out by several recrystallizations from isopropanol

Sources & evidence

ORD record
ord-b2427ecff39049ad9e450e5d63f62cf2
Source dataset
uspto-grants-1976_06
Patent number
US03963313

Reaction notes

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