p-Toluenesulfonic acid → 88450-60-6

HRID 2418689Notes

Reaction equation

HRID 2418689 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[Cl:11][C:12]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:13]=1[NH2:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N:14][C:13]1[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:12]=1[Cl:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 111232,4-DichloroanilineHCID 618142,4-Dimethylbenzaldehyde

Product 1

HCID 1333998888450-60-6

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 26.8 g. of 2,4-dimethylbenzaldehyde, 32.4 g. of 2,4-dichloroaniline, 0.20 g. of p-toluenesulfonic acid, and 150 ml of toluene is stirred under reflux using a Dean-Stark moisture trap. Evaporation of the mixture affords a solid which is recrystallized from ethanol to yield N-(2,4-dimethylbenzylidene)-2,4-dichloroaniline, mp 102°-106°.

Workup

  1. additionA mixture of 26.8 g
  2. temperatureunder reflux
  3. customEvaporation of the mixture
  4. customaffords a solid which
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-f60acec866b94558b4c5697b721baa83
Source dataset
uspto-grants-1984_09
Patent number
US04473579

Reaction notes

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