Oxalic Acid → 6,7-Bis(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione

HRID 54399Notes

Reaction equation

HRID 54399 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([NH2:13])=[C:5]([NH2:14])[CH:4]=1.[C:17](O)(=[O:21])[C:18](O)=[O:19]>Cl>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10])[NH:13][C:18](=[O:19])[C:17](=[O:21])[NH:14]2

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 40613654,5-Bis(trifluoromethyl)benzene-1,2-diamine

Product 1

HCID 211900176,7-Bis(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dioneYield 35.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 102 mg (0.418 mmol) of 4,5-bis(trifluoromethyl)-1,2-phenylenediamine and 37 mg (0.411 mmol) of oxalic acid in 2 mL of 2N HCl was refluxed for 6 h and cooled to room temperature. The mixture was filtered and washed by water, CHCl3 and dried to leave a colorless solid (43 mg, 35%), mp>250° C. 1H NMR (DMSO-d6), 7.629 (s, 2) 12.293 (s, 2). 19F NMR (DMSO-d6), 62.185 (s).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationThe mixture was filtered
  3. washwashed by water, CHCl3
  4. customdried

Sources & evidence

ORD record
ord-418d4b335c024a97961dfc7664c73bea
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Reaction notes

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