p-Toluenesulfonic acid → 49763-59-9

HRID 1439146Notes

Reaction equation

HRID 1439146 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:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[CH2:11][CH2:12][CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:10]([C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:20][CH:21]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 133964-AminobenzonitrileHCID 709884-Butylbenzaldehyde

Product 1

HCID 2336911849763-59-9

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 11.8 g. of p-aminobenzonitrile and 16.2 g. of p-n-butylbenzaldehyde in 200 ml. of benzene is treated with 300 mg. of p-toluenesulfonic acid and reacted as described in Example 1. After the addition of 3 g. of solid potassium carbonate, the mixture is filtered and evaporated, whereby there are obtained 27.0 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-butylbenzyliden)amino]benzonitrile which is obtained has a melting point of 38.1°-38.7° C. and a clearing point of 62.6° C. UV (ethanol): ε280 = 24900 (shoulder at 314 nm). The nuclear magnetic resonance, mass spectrum, infrared and microanalysis data confirm the structure.

Workup

  1. additionA mixture of 11.8 g
  2. additionAfter the addition of 3 g
  3. filtrationof solid potassium carbonate, the mixture is filtered
  4. customevaporated
  5. customwhereby there are obtained 27.0 g
  6. customof a yellow oil which crystallizes
  7. temperaturewith cooling
  8. customPurification
  9. customis carried out by several recrystallizations from isopropanol

Sources & evidence

ORD record
ord-a1efd47b9dc947f49598fcc1f3d4a971
Source dataset
uspto-grants-1977_11
Patent number
US04058477

Reaction notes

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