4-Trifluoromethyl-1,2-phenylenediamine → 1,4-Dihydro-6-(trifluoromethyl)-2,3-quinoxalinedione

HRID 1658049Notes

Reaction equation

HRID 1658049 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.[C:13](OCC)(=[O:17])[C:14]([O-])=[O:15]>>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][C:14](=[O:15])[C:13](=[O:17])[NH:10]2

Participants

3

Reactant 2

HCID 5208224-Trifluoromethyl-1,2-phenylenediamineHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 1913821,4-Dihydro-6-(trifluoromethyl)-2,3-quinoxalinedione

Procedure

4-Trifluoromethyl-o-phenylenediamine (8.0 grams) was added to 80 ml. of ethyl oxalate and the resulting mixture was heated to reflux and refluxed for two hours. A precipitate formed during this period. The reaction mixture was then cooled to room temperature and filtered to separate the precipitate, m.p. 344°-346°C. (dec.) The product was identified as the expected 6-trifluoromethyl- 2(1H), 3(4H)-quinoxalinedione, by IR, TLC, NMR, and microanalysis.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for two hours
  3. customA precipitate formed during this period
  4. filtrationfiltered
  5. customto separate the precipitate, m.p. 344°-346°C. (dec.) The product

Sources & evidence

ORD record
ord-59abf0883b5d4153b84d01a9b52db743
Source dataset
uspto-grants-1976_06
Patent number
US03962440

Reaction notes

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