Hydrochloric Acid → N-(3,5-dichloro-2-pyridyl)-2,6-dinitro-3-chloro-4-trifluoromethylaniline

HRID 1065773Notes

Reaction equation

HRID 1065773 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH-].[K+].[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[C:26]([F:29])([F:28])[F:27].Cl>O.CN(C)C=O>[Cl:8][C:7]1[C:2]([NH:1][C:17]2[C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]([C:26]([F:27])([F:28])[F:29])=[C:13]([Cl:12])[C:18]=2[N+:19]([O-:21])=[O:20])=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 778863,5-Dichloro-3-pyridylamineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 12812469N-(3,5-dichloro-2-pyridyl)-2,6-dinitro-3-chloro-4-trifluoromethylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 20 ml. of dimethylformamide, 1.63 g. of 2-amino-3,5-dichloropyridine was dissolved and 0.73 g. of powdery potassium hydroxide was added with stirring. After the addition, 3.06 g. of 2,4-dichloro-3,5-dinitrobenzotrifluoride was added during 10 minutes. The reaction was continued for about 2 hours. After the reaction, the reaction mixture was poured into water and acidified with conc. HCl and the product was extracted with methylene chloride. The extracted layer was washed with water and dehydrated and the solvent was distilled off and the product was separated by a silica gel column with an eluent of toluene and then the solvent was distilled off to obtain 1.38 g. of the object compound having the melting point of 64° to 65° C.

Workup

  1. additionAfter the addition, 3.06 g
  2. customAfter the reaction
  3. extractionthe product was extracted with methylene chloride
  4. washThe extracted layer was washed with water
  5. distillationthe solvent was distilled off
  6. customthe product was separated by a silica gel column with an eluent of toluene
  7. distillationthe solvent was distilled off
  8. customto obtain 1.38 g

Sources & evidence

ORD record
ord-3491617f45c3462aa8a03b9dbced7e2e
Source dataset
uspto-grants-1982_05
Patent number
US04331670

Reaction notes

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