Ethanedioyl dibromide → HCID 58432792, compound

HRID 1958305Notes

Reaction equation

HRID 1958305 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5](=O)[NH:4][CH:3]=1.C(Br)(=O)C([Br:23])=O>CN(C=O)C.ClCCCl>[Br:23][C:5]1[C:6](=[O:18])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:2]([CH3:1])=[CH:3][N:4]=1

Participants

5

Reactant 2

HCID 84841Ethanedioyl dibromide2×HCID 59564946HCID 59564946, compound

Product 1

HCID 58432792HCID 58432792, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalyst2×HCID 111,2-DichloroethaneSolvent

Procedure

6-Methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrazine-2,3-dione (0.52 g, 1.92 mmol) and 1,2-dichloroethane (10 ml) were placed in a vial (20 ml). To the resulting suspension was added carefully oxalyl bromide (0.53 ml, 1.24 g, 5.75 mmol). A foam was formed during the addition, and as the foam was settling down the stirring was started. DMF (3 drops) was added and the vial was sealed and the mixture was stirred overnight. Another portion of oxalyl bromide (0.2 ml, 0.46 g, 2.23 mmol) and DMF (3 drops) was added and the reaction was run for another 24 h. The mixture was partitioned between DCM (20 ml) and water (20 ml) and the organic phase was dried. Filtration and evaporation gave a crude product, which was purified on silica, affording 0.59 g (93%) of 3-bromo-6-methyl-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one.

Workup

  1. customA foam was formed during the addition
  2. customthe vial was sealed
  3. waitthe reaction was run for another 24 h
  4. customThe mixture was partitioned between DCM (20 ml) and water (20 ml)
  5. customthe organic phase was dried
  6. filtrationFiltration and evaporation
  7. customgave a crude product, which
  8. customwas purified on silica

Sources & evidence

ORD record
ord-4896f1ba4c984260b24f2d87cbc7e914
Source dataset
uspto-grants-2013_04
Patent number
US08410114B2

Reaction notes

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