4-Chloro-2-toluidine → N-(p-Chlorobenzylidene)-2-methyl-4-chloroaniline

HRID 261826Notes

Reaction equation

HRID 261826 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[N:4][C:3]2[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=2[CH3:1])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 77264-Chlorobenzaldehyde

Product 1

HCID 13017552N-(p-Chlorobenzylidene)-2-methyl-4-chloroaniline

Procedure

2-Methyl-4-chloroaniline (0.25 mole) and 4-chlorobenzaldehyde (0.25 mole) are ground in a mortar. The mixture is heated, with stirring in a water bath for 1.5 hrs. Distillation at reduced pressure gives N-(p-Chlorobenzylidene)-2-methyl-4-chloroaniline. b.p. 139° C./0.020 mm.

Workup

  1. temperatureThe mixture is heated
  2. distillationDistillation at reduced pressure

Sources & evidence

ORD record
ord-431d88173194447ba969f11ee36f4fb1
Source dataset
uspto-grants-1979_05
Patent number
US04152452

Reaction notes

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