Diethyl Oxalate → 6-Chloro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 1458583Notes

Reaction equation

HRID 1458583 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([Cl:12])=[CH:4][C:3]=1[NH2:13].[C:14](OCC)(=[O:20])[C:15](OCC)=[O:16]>>[Cl:12][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[C:8]([F:9])([F:10])[F:11])[NH:1][C:15](=[O:16])[C:14](=[O:20])[NH:13]2

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 27734974-Chloro-5-(trifluoromethyl)benzene-1,2-diamine

Product 1

HCID 106116896-Chloro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedioneYield 86%

Procedure

A mixture of 1,2-diamino-4-chloro-5-trifluoromethylbenzene (13.4 g, 63.6 mmol) and diethyl oxalate (100 ml) was heated at reflux under nitrogen with stirring for 5 h. After being cooled, the solid which formed was filtered off and washed well with ether to afford a pale orange solid (14.5 g, 86%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen
  3. temperatureAfter being cooled
  4. customthe solid which formed
  5. filtrationwas filtered off
  6. washwashed well with ether

Sources & evidence

ORD record
ord-2f097fd290bc45fca72ccd7e2a84b257
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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