3-Chloro-2-methylaniline → N-(p-chlorobenzylidene)-2-methyl-3-chloroaniline

HRID 47091

Reaction equation

HRID 47091 reaction equation
[CH3:1][C:2]1[C:8]([Cl:9])=[CH:7][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][CH:7]=[C:8]([Cl:9])[C:2]=2[CH3:1])=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 77264-Chlorobenzaldehyde

Product 1

HCID 13017553N-(p-chlorobenzylidene)-2-methyl-3-chloroaniline

Procedure

2-methyl-3-chloroaniline (0.25 mole) and 4-chlorobenzaldehyde (0.25 mole) were ground in a mortar. The mixture was heated, with stirring in a water bath for 1.5 hours. Distillation at reduced pressure gave N-(p-chlorobenzylidene)-2-methyl-3-chloroaniline as a second fraction; B.p. 139° C./0.020 mm.; m.p. 79°-81° C.

Workup

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

Sources & evidence

ORD record
ord-1954ed2e6b654a29afa1d9e4851e850b
Source dataset
uspto-grants-1979_11
Patent number
US04176198

Linked notes

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