Hydrochloric Acid → 3,5-Dichloro-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-2-pyridinamine

HRID 1065775Notes

Reaction equation

HRID 1065775 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH-].[K+].[N+:12]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([C:24]([F:27])([F:26])[F:25])[C:16]=1Cl)([O-:14])=[O:13].Cl>CN(C)C=O>[Cl:8][C:7]1[C:2]([NH:1][C:16]2[C:17]([C:24]([F:26])([F:27])[F:25])=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 778863,5-Dichloro-3-pyridylamine

Product 1

HCID 129016033,5-Dichloro-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml. of dimethylformamide, 1.65 g. of 2-amino-3,5-dichloropyridine was dissolved and 1.0 g. of powdery potassium hydroxide was gradually added with stirring. After the addition, 2.7 g. of 2,4-dinitro-6-trifluoromethylchlorobenzene was added at 30° C. during 5 minutes to react them for about 3 hours. The reaction mixture was acidified with conc. HCl and the product was extracted with methylenechloride. The extracted layer was washed with water and dehydrated and the solvent was distilled. The product was separated by a silica gel column with an eluent of toluene and the solvent was distilled off to obtain 2.5 g. of the object compound having the melting point of 98° to 101° C.

Workup

  1. additionAfter the addition, 2.7 g
  2. customto react them for about 3 hours
  3. extractionthe product was extracted with methylenechloride
  4. washThe extracted layer was washed with water
  5. distillationthe solvent was distilled
  6. customThe product was separated by a silica gel column with an eluent of toluene
  7. distillationthe solvent was distilled off
  8. customto obtain 2.5 g

Sources & evidence

ORD record
ord-043b4204da8040d5ae03f1aa5352abee
Source dataset
uspto-grants-1982_05
Patent number
US04331670

Reaction notes

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