Benzenamine, 2-chloro-5-(trifluoromethyl)- → N-(2,2-dicyanovinyl)-2-chloro-5-trifluoromethylaniline

HRID 26707

Reaction equation

HRID 26707 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1[NH2:4].C(O[CH:16]=[C:17]([C:20]#[N:21])[C:18]#[N:19])C>C(O)C>[C:18]([C:17]([C:20]#[N:21])=[CH:16][NH:4][C:3]1[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[CH:7]=[CH:8][C:2]=1[Cl:1])#[N:19]

Participants

4

Reactant 2

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 671522-(Ethoxymethylene)propanedinitrile

Product 1

HCID 21322397N-(2,2-dicyanovinyl)-2-chloro-5-trifluoromethylanilineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19.6 Parts of 2-chloro-5-trifluoromethyl-aniline and 12.2 parts of ethoxymethylenemalononitrile are dissolved in 125 parts of ethanol and the mixture is refluxed for 48 hours. After cooling, the precipitated product is collected by filtration and washed with ethanol. Recrystallisation from ethanol affords the above product with a melting point of 166°-169° C. and in a 70% yield.

Workup

  1. temperaturethe mixture is refluxed for 48 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated product is collected by filtration
  4. washwashed with ethanol
  5. customRecrystallisation from ethanol
  6. customaffords the above product with a melting point of 166°-169° C.

Sources & evidence

ORD record
ord-bc92207860594f63ba30a4e98edc8c79
Source dataset
uspto-grants-1979_04
Patent number
US04151298

Linked notes

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