Water → 1-(3-Chloro-2,6-dinitro-4-trifluoromethylphenyl)-4-trifluoromethylpyrimidin-6-one

HRID 1461733Notes

Reaction equation

HRID 1461733 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:4]=[CH:5][NH:6][C:7](=[O:9])[CH:8]=1.[Cl:12][C:13]1(F)[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]1(F)F.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:12][C:13]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([N:6]2[C:7](=[O:9])[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[N:4]=[CH:5]2)[C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[C:2]([F:11])([F:10])[F:1]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1317171362,4-Dichloro-3,5-dinitrotrifluorobenzeneHCID 1354586204-Hydroxy-6-(trifluoromethyl)pyrimidine

Product 1

HCID 198771631-(3-Chloro-2,6-dinitro-4-trifluoromethylphenyl)-4-trifluoromethylpyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-trifluoromethylpyrimidin-6-one (0.48 g), 2,4-dichloro-3,5-dinitrotrifluorobenzene (0.9 g) and potassium carbonate (0.41 g) in dry dimethylformamide (10 ml) was vigorously stirred at ambient temperature for a period of 15 minutes. The reaction mixture was then poured into water, and extracted into ethyl acetate. After drying and evaporation of the solvent, under reduced pressure, the residue was subjected to chromatography on silica gel using 30% (by volume) ethylacetate in petroleum ether (boiling range 60°-80° C.) as eluent. The required fractions were combined, and the solvent removed under reduced pressure to give a yellow solid, which was then triturated with petroleum ether (boiling range 60°-80° C.). The solid was dissolved in boiling ethanol, filtered, and the solvent removed under reduced pressure. The residue was again triturated with petroleum ether (boiling range 60°-80° C.) and finally recrystallised from petroleum ether (boiling range 60°-80° C.) containing ethylacetate (9% by volume) to give 1-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-4-trifluoromethylpyrimidin-6-one as a yellow solid:

Workup

  1. extractionextracted into ethyl acetate
  2. customAfter drying
  3. customevaporation of the solvent
  4. customthe solvent removed under reduced pressure
  5. customto give a yellow solid, which
  6. customwas then triturated with petroleum ether (boiling range 60°-80° C.)
  7. dissolutionThe solid was dissolved
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customThe residue was again triturated with petroleum ether (boiling range 60°-80° C.)
  11. customfinally recrystallised from petroleum ether (boiling range 60°-80° C.)
  12. additioncontaining ethylacetate (9% by volume)

Sources & evidence

ORD record
ord-8369dec94a844094b2679810272dc9a9
Source dataset
uspto-grants-1991_12
Patent number
US05077297

Reaction notes

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