Dimethylformamide → 6-pentafluoroethyl-2(1H), 3(4H)-quinoxalinedione

HRID 2285863Notes

Reaction equation

HRID 2285863 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3](=[O:11])[C:2]1=[O:12].FC(F)(F)S([O-])(=O)=O.[F:21][C:22]([I+]C1C=CC=CC=1)([F:27])[C:23]([F:26])([F:25])[F:24].CN(C)C=O>C(OCC)(=O)C>[F:21][C:22]([F:27])([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:11])[C:2](=[O:12])[NH:1]2)[C:23]([F:26])([F:25])[F:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 274912,3-DihydroxyquinoxalineHCID 11488264Pentafluoroethylphenyliodonium trifluoromethanesulfonate

Product 1

HCID 128719856-pentafluoroethyl-2(1H), 3(4H)-quinoxalinedioneYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 0.5 g of 2(1H), 3(4H)-quinoxalinedione, 1.60 g of pentafluoroethylphenyliodonium trifluoromethanesulfonate and 10 ml of dimethylformamide was stirred overnight on an oil bath at 45° C. Ethyl acetate was then added to the reaction mixture and the unreacted 2(1H), 3(4H)-quinoxalinedione was removed by filtration (recovery of the starting material: 0.13 g). Water was added to the filtrate and, after rendering the mixture neutral, the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and the solvent was distilled off. A small amount of methylene chloride was added to the residue and the precipitated crystals were collected by filtration to obtain 0.05 g of 6-pentafluoroethyl-2(1H), 3(4H)-quinoxalinedione as colorless crystals. Yield 6% (conversion yield, 8%). Melting Point (after recrystallized from acetonitrile): 317°-320° C. (with decomposition).

Workup

  1. customthe unreacted 2(1H), 3(4H)-quinoxalinedione was removed by filtration (recovery of the starting material
  2. additionWater was added to the filtrate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. additionA small amount of methylene chloride was added to the residue
  8. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-31ab1b098c5046459aab17fe543cf85c
Source dataset
uspto-grants-1982_04
Patent number
US04324741

Reaction notes

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