4-Chloroaniline → HCID 22769691, compound

HRID 1764736Notes

Reaction equation

HRID 1764736 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:11]=1[C:22]([F:25])([F:24])[F:23]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][C:11]=2[C:22]([F:23])([F:25])[F:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-

Product 1

HCID 22769691HCID 22769691, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloroaniline (127.5 g) and 2-chloro-3,5-dinitrobenzotrifluoride (270.5 g.) in toluene (2 l.) was heated under reflux for 16 hours and the hot mixture then filtered. The filtrate was concentrated in vacuo, and the true amounts of toluene removed by co-distillation with industrial methylated spirit, to give a black semi-solid. Extraction of this solid with cyclohexane gave yellow crystals of 2(4-chloroanilino)-3,5-dinitrobenzotrifluoride, melting point 104°-106° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. filtrationthe hot mixture then filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe true amounts of toluene removed by co-distillation with industrial methylated spirit
  6. customto give a black semi-solid
  7. extractionExtraction of this solid with cyclohexane

Sources & evidence

ORD record
ord-129e12dfbe8f496796c95fa37e09d449
Source dataset
uspto-grants-1978_09
Patent number
US04117167

Reaction notes

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