Pyridine → 2',6'-Dinitro-4'-trifluoromethyl-2,2,2-trifluoroacetanilide

HRID 1576377Notes

Reaction equation

HRID 1576377 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:5]=1[NH2:6])([O-:3])=[O:2].N1C=CC=CC=1.[F:24][C:25]([F:30])([F:29])[C:26](Cl)=[O:27].FC(F)(F)C(O)=O>C(O)C>[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:5]=1[NH:6][C:26](=[O:27])[C:25]([F:30])([F:29])[F:24])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 99362,6-Dinitro-4-(trifluoromethyl)anilineHCID 61106Trifluoroacetyl chloride

Product 1

HCID 215124262',6'-Dinitro-4'-trifluoromethyl-2,2,2-trifluoroacetanilide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 25.1 g. of 2,6-dinitro-4-trifluoromethylaniline in 100 ml. of pyridine was treated with trifluoroacetyl chloride, which has been prepared from 10 ml. of trifluoroacetic acid. Ethanol was added to the resulting mixture until it was homogeneous, and the reaction mixture was then evaporated under vacuum. The residue after evaporation was washed with water, dried, dissolved in acetone, and filtered. Chloroform was added to the filtrate until the product precipitated. The precipitate was separated by filtration and dried to obtain the purified intermediate, 2',6'-dinitro-4'-trifluoromethyl-2,2,2-trifluoroacetanilide.

Workup

  1. customhas been prepared from 10 ml
  2. customthe reaction mixture was then evaporated under vacuum
  3. customThe residue after evaporation
  4. washwas washed with water
  5. customdried
  6. dissolutiondissolved in acetone
  7. filtrationfiltered
  8. additionChloroform was added to the filtrate until the product
  9. customprecipitated
  10. customThe precipitate was separated by filtration
  11. customdried

Sources & evidence

ORD record
ord-2acf227a1cfb4dcdbbbcc2e56b5f5bcc
Source dataset
uspto-grants-1976_09
Patent number
US03980784

Reaction notes

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