p-Toluenesulfonic acid → HCID 13796483, compound

HRID 1439150Notes

Reaction equation

HRID 1439150 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:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 2734685Benzaldehyde, 4-octyl-

Product 1

HCID 13796483HCID 13796483, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.9 g. of p-aminobenzonitrile and 10.9 g. of p-n-octylbenzaldehyde in 100 ml. of benzene is treated with 150 ml. of p-toluenesulfonic acid and reacted as described in Example 1. After evaporation, there remain 16.5 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-octylbenzyliden)amino]benzonitrile which is obtained has a melting point of 32.5°-32.8° C. and a clearing point of 68.8° C. Up to 54.4° C. the compound is smectic. UV (ethanol): ε280 = 24200 (shoulder at 312 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-e90d1dd01b02444ca2ae986dea3642f4
Source dataset
uspto-grants-1977_11
Patent number
US04058477

Reaction notes

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