p-Toluenesulfonic acid → Benzonitrile, 4-(((4-hexylphenyl)methylene)amino)-

HRID 1439148

Reaction equation

HRID 1439148 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:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 170813Benzaldehyde, 4-hexyl-

Product 1

HCID 170099Benzonitrile, 4-(((4-hexylphenyl)methylene)amino)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.9 g. of p-aminobenzonitrile and 9.5 g. of p-n-hexylbenzaldehyde 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 14.4 g. of a brownish oil which crystallizes with cooling. Purification is carried out by several recrystallizations from isopropanol as described in Example 1. The p-[(p-n-hexylbenzyliden)amino]benzonitrile which is obtained has a melting point of 32.2°-33.0° C. and a clearing point of 64.5° C. UV (ethanol): ε281 = 23500 (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 brownish oil which crystallizes
  4. temperaturewith cooling
  5. customPurification
  6. customis carried out by several recrystallizations from isopropanol

Sources & evidence

ORD record
ord-e402a2a3f42a44bfb3e50e01f85ba59f
Source dataset
uspto-grants-1977_11
Patent number
US04058477

Linked notes

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