N-bromobutanimide → HCID 118599075, compound

HRID 1050406Notes

Reaction equation

HRID 1050406 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5](=[O:8])[NH:4][C:3]=1[C:9]([O:11][CH3:12])=[O:10].[Br:13]N1C(=O)CCC1=O>ClCCl>[Br:13][C:6]1[C:5](=[O:8])[NH:4][C:3]([C:9]([O:11][CH3:12])=[O:10])=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57992080HCID 57992080, compound

Product 1

HCID 118599075HCID 118599075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3-methyl-6-oxo-1,6-dihydropyrazine-2-carboxylate (2.0 g, 11.89 mmol) was dissolved in dichloromethane (30 mL) and N-bromosuccinimide (2.12 g, 11.89 mmol) was added. The reaction was allowed to stir at room temperature for 16 h. On completion, the reaction mixture was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The solid was washed with ether to afford methyl 5-bromo-3-methyl-6-oxo-1,6-dihydropyrazine-2-carboxylate (2) as light brown solid. Yield: 1.25 g, 42%; MS (ESI) m/z 247.04 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 12.92 (brs, 1H), 3.87 (s, 4H), 2.50 (s, 3H).

Workup

  1. washOn completion, the reaction mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe solid was washed with ether

Sources & evidence

ORD record
ord-b10dcf86858f4d7f89e4ff066e4e9f96
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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