Diethyl Oxalate → 5-Bromo-7-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione

HRID 439449Notes

Reaction equation

HRID 439449 reaction equation
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Br:22])[C:13]=1[NH2:23]>>[Br:22][C:14]1[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=[C:12]2[C:13]=1[NH:23][C:2](=[O:4])[C:1](=[O:8])[NH:11]2

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 7357853-Bromo-4,5-diaminobenzotrifluoride

Product 1

HCID 28014475-Bromo-7-(trifluoromethyl)-1,4-dihydroquinoxaline-2,3-dione

Procedure

The title compound was prepared using an adaptation of the method of Cheeseman, G. W. H., J. Chem. Soc. 1171 (1962). A mixture of diethyl oxalate (1.15 g, 7.91 mmol) and 1,2-diamino-3-bromo-5-trifluoromethylbenzene (200 mg, 0.95 mmol) was heated to reflux under N2 for 2 h. The reaction was allowed to cool to room temperature and the solid collected by vacuum filtration and rinsed with EtOH (15 mL). This white solid was dried in a drying pistol (0.05 torr, 78° C.) to yield 148.3 mg (60.7%). mp 301-304 (dec). 1H NMR (d6 -DMSO) δ7.28 (s, 1H, ArH), 7.56 (s, 1H, ArH), 11.7 (br s, 2H, NH). 19F NMR (C6F6 external standard, δ-162.9) δ-57.97 (s). EIHRMS calc. for C9H4BrF3N2O2 307.9408, found 307.9411.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 2 h
  3. filtrationthe solid collected by vacuum filtration
  4. washrinsed with EtOH (15 mL)
  5. customThis white solid was dried in a drying pistol (0.05 torr, 78° C.)
  6. customto yield 148.3 mg (60.7%)

Sources & evidence

ORD record
ord-13a8be5e404545e8927465e39193c2df
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Reaction notes

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