Hydrochloric Acid → 2-Pyridinamine, 3,5-dichloro-N-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-6-methyl-

HRID 1065772Notes

Reaction equation

HRID 1065772 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([CH3:10])[N:3]=1.[OH-].[K+].[Cl:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18](Cl)[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]=1[C:27]([F:30])([F:29])[F:28].Cl>O.CN(C)C=O>[Cl:8][C:7]1[C:2]([NH:1][C:18]2[C:17]([N+:24]([O-:26])=[O:25])=[CH:16][C:15]([C:27]([F:28])([F:29])[F:30])=[C:14]([Cl:13])[C:19]=2[N+:20]([O-:22])=[O:21])=[N:3][C:4]([CH3:10])=[C:5]([Cl:9])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzeneHCID 14158632-Amino-3,5-dichloro-6-methylpyridine

Product 1

HCID 1575402-Pyridinamine, 3,5-dichloro-N-(3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl)-6-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In 30 ml. of dimethylformamide, 1.8 g. of 2-amino-3,5-dichloro-6-methylpyridine was dissolved in 0.67 g. of powdery potassium hydroxide was gradually added with stirring. After the addition, a solution of 3.07 g. of 2,4-dichloro-3,5-dinitrobenzotrifluoride in 10 ml. of dimethylformamide was added dropwise at room temperature and the reaction was continued for about 3 hours. The reaction mixture was acidified with conc. HCl and was poured into water. The precipitate was filtered and recrystallized from methanol to obtain 2.96 g. of the object compound having a melting point of 128° to 130° C.

Workup

  1. additionAfter the addition
  2. filtrationThe precipitate was filtered
  3. customrecrystallized from methanol
  4. customto obtain 2.96 g

Sources & evidence

ORD record
ord-06c44d3f20044cb5846138d3ba1823a7
Source dataset
uspto-grants-1982_05
Patent number
US04331670

Reaction notes

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