Benzaldehyde → N-benzylidene-3,5-dichloroaniline

HRID 1111882

Reaction equation

HRID 1111882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[N:5]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 297MethaneHCID 122813,5-DichloroanilineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 962139N-benzylidene-3,5-dichloroaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a reaction flask, equipped with a Dean-Stark trap, is added 3,5-dichloroaniline (16.2 g., 0.10 mole), benzaldehyde (10.6 g., 0.10 mole), p-toluenesulfonic acid monohydrate (0.2 g.), and toluene (100 ml.). The reaction mixture is then warmed to reflux and the water (1.65 ml.) collected by azeotroping. The cooled reaction mixture is treated with charcoal and the filtrate reduced in vacuo to give an amber oil, that crystallizes on standing to give 24.6 g. of product, which is recrystallized from pentane to give 18.5 g. of yellow solid, m.p. 52°-53° C.

Workup

  1. customTo a reaction flask, equipped with a Dean-Stark trap
  2. temperatureThe reaction mixture is then warmed
  3. temperatureto reflux
  4. customthe water (1.65 ml.) collected
  5. customby azeotroping
  6. customThe cooled reaction mixture
  7. customto give an amber oil
  8. customthat crystallizes
  9. customto give 24.6 g
  10. customof product, which is recrystallized from pentane
  11. customto give 18.5 g

Sources & evidence

ORD record
ord-d819304fe79846659f848e04ba34e100
Source dataset
uspto-grants-1978_10
Patent number
US04119667

Linked notes

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