Dimethylformamide → 3-Bromo-5-phenylpyrazin-2(1H)-one

HRID 1747777Notes

Reaction equation

HRID 1747777 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10](=[O:13])[NH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.CN(C=O)C>O>[Br:14][C:9]1[C:10](=[O:13])[NH:11][CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 5990375-phenyl-1H-pyrazin-2-one

Product 1

HCID 124535473-Bromo-5-phenylpyrazin-2(1H)-oneYield 14.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-phenylpyrazin-2(1H)-one (0.86 g), N-bromosuccinimide (0.89 g) and DMF (16 mL) was stirred at room temperature for 2 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give the title compound (0.18 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-e3f95176644442dd8ee68b8a0625502d
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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