Water → 5-Bromo-3-chloropyrazin-2-amine

HRID 2387225Notes

Reaction equation

HRID 2387225 reaction equation
[Cl:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:15]Br.O>C(O)(=O)C>[Br:15][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([NH2:8])=[N:4][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium Carbonate2×HCID 24408Bromine2×HCID 2762242-Amino-3-chloropyrazine

Product 1

HCID 467382025-Bromo-3-chloropyrazin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

3-Chloro-pyrazin-2-ylamine (0.750 g, 5.79 mmol) is suspended in acetic acid (7 ml) with stirring at room temperature and sodium carbonate (0.675 g, 6.37 mmol) is added. When all the gas has evolved bromine (0.171 ml, 3.34 mmol) in acetic acid (4 ml) is added dropwise. Sodium carbonate (0.675 g, 6.37 mmol) is added and a gas evolves. Once all gas has evolved bromine (0.171 ml, 3.34 mmol) in acetic acid (4 ml) is added. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is poured onto iced water and left to stir for 30 minutes. A pale yellow suspension has formed. This solid is filtered off and rinsed with cold water to give 5-Bromo-3-chloro-pyrazin-2-ylamine.

Workup

  1. additionis added dropwise
  2. additionis added
  3. stirringThe reaction mixture is stirred at room temperature for 1 hour
  4. waitleft
  5. stirringto stir for 30 minutes
  6. customA pale yellow suspension has formed
  7. filtrationThis solid is filtered off
  8. washrinsed with cold water

Sources & evidence

ORD record
ord-f9f1d3d157f7446ab1b5ecad41372fca
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

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