Water → 3-[4-(Butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

HRID 849923

Reaction equation

HRID 849923 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]1[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:17]=1.[F-].[K+].[C:26]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])(=[O:29])[CH2:27][OH:28].O>O1CCOCC1>[CH2:31]([O:30][C:26]([CH2:27][O:28][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][N:17]=2)=[C:2]([F:1])[CH:7]=1)=[O:29])[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 81882Butyl GlycolateHCID 522689Potassium FluorideHCID 193654873-(2,4-Difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine2×

Product 1

HCID 193654963-[4-(Butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazineYield 82.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Then, 7.61 g of 3-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-16) was dissolved in 10 ml of 1,4-dioxane, to which 5.28 g of potassium fluoride and 9.0 g of butyl glycolate were added, and the mixture was heated under reflux for 1.5 hours. After completion of the reaction, the reaction mixture was left cooling to room temperature. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 8.37 g (yield, 82%) of 3-[4-(butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (the present compound depicted below; m.p., 109.5° C.). ##STR40##

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1.5 hours
  4. customAfter completion of the reaction
  5. waitthe reaction mixture was left
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6a9cb36e4f8242a090d57dc7fe78646f
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Linked notes

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