p-Toluenesulfonic acid → HCID 12239366, compound

HRID 1658159Notes

Reaction equation

HRID 1658159 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:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 208614-Ethylbenzaldehyde

Product 1

HCID 12239366HCID 12239366, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5.9 g. of p-aminobenzonitrile and 6.7 g. of p-ethylbenzaldehyde in 100 ml. of benzene is treated with 150 mg. of p-toluenesulfonic acid, gassed with nitrogen and heated at reflux for 1 hour (bath temperature 120°C.). The water which forms is separated by means of a water separator. During an additional 1 hour of refluxing, the benzene which condenses in the reflux condenser is led back to the reaction vessel through a layer of 50 g. of aluminum oxide (activity I). After cooling, 2 g. of solid potassium carbonate are added. The mixture is filtered and the filtrate freed from the solvent under vacuum at 50°C. (bath temperature), whereby there remains 11.5 g. of a yellow oil which crystallizes with cooling. Purification is carried out by several recrystallizations from isopropanol to a constant melting point and until by-products are no longer observed by gas chromatogram. The p-[(p-ethylbenzyliden)amino]benzonitrile which is obtained melts at 76.2°-77.0°C. and is liquid crystalline with cooling from 63.0°-59.7°C. UV (ethanol): ε277 = 25800 (shoulder at 316 nm). The nuclear magnetic resonance, mass spectrum, infrared and microanalysis date confirm the structure.

Workup

  1. additionA mixture of 5.9 g
  2. temperatureheated
  3. customThe water which forms is separated by means of a water separator
  4. temperatureDuring an additional 1 hour of refluxing
  5. temperatureAfter cooling
  6. additionof solid potassium carbonate are added
  7. filtrationThe mixture is filtered
  8. customfreed from the solvent under vacuum at 50°C.
  9. customof a yellow oil which crystallizes
  10. temperaturewith cooling
  11. customPurification
  12. customis carried out by several recrystallizations from isopropanol to a constant melting point and until by-products

Sources & evidence

ORD record
ord-362bd82838864f1c8e38433343f515bf
Source dataset
uspto-grants-1976_06
Patent number
US03963313

Reaction notes

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