4-Chloroaniline → ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]propionate

HRID 2058086Notes

Reaction equation

HRID 2058086 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C1C=CC=CC=1>[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([N:22]=[CH:1][C:3]2[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 3016639Ethyl 2-(4-formylphenoxy)propionate

Product 1

HCID 14871451ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]propionateYield 94.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(a) In 100 ml of dried benzene are dissolved 17.0 g of ethyl 2-(4-formylphenoxy)propionate and 9.73 g of 4-chloroaniline, and the mixture is refluxed under heating and with stirring for 6 hours. Concentration of the reaction mixture gives 24.0 g of ethyl 2-[4-{N-(4-chlorophenyl)formimidoyl}phenoxy]propionate as an oily product.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating

Sources & evidence

ORD record
ord-277aef7aca204c249b5dec4be14fdf7b
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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