4-Chloroaniline → Methyl 4-[[(4-chlorophenyl)imino]methyl]benzoate

HRID 1414173Notes

Reaction equation

HRID 1414173 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C(O)C>[CH3:4][O:3][C:1](=[O:2])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:18][C:17]2[CH:19]=[CH:20][C:14]([Cl:13])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 101086Methyl 4-[[(4-chlorophenyl)imino]methyl]benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

165 g (1 mole) of 4-carbomethoxybenzaldehyde and 128 g (1 mole) of 4-chloroaniline were stirred in 2500 ml of ethanol for 3 hours on a weak reflux, when cooled to -10°C, filtered with suction and washed with ethanol having a temperature of -10° C. After drying, 227 g (83% of the theory) of 4-(p-chlorophenylimino-methyl)-benzoicacid methyl ester of the following formula were obtained ##STR42##

Workup

  1. filtrationfiltered with suction
  2. washwashed with ethanol having a temperature of -10° C
  3. customAfter drying

Sources & evidence

ORD record
ord-342240c6efd74bca9afe3daa57333fd0
Source dataset
uspto-grants-1977_01
Patent number
US04001221

Reaction notes

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