N-bromobutanimide → 5-Bromo-6-chloropyrazin-2-amine

HRID 343373Notes

Reaction equation

HRID 343373 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:7]=[N:6][C:5]([Br:9])=[C:4]([Cl:8])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1184582-Amino-6-Chloropyrazine

Product 1

HCID 181802075-Bromo-6-chloropyrazin-2-amineYield 18.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-amino-6-chloropyrazine (5.0 g) and N-bromosuccinimide (13.9 g) in chloroform (200 ml) was heated under reflux for 2 hours. Insoluble material was removed by filtration and the filtrate was concentrated by evaporation. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane, to give 2-amino-5-bromo-6-chloropyrazine (1.5 g); m.p. 120°-122° C.; mass spectrum (+ve CI): 208 (M+H)+.

Workup

  1. temperatureunder reflux for 2 hours
  2. customInsoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated by evaporation
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6ad7ec9cc5714a45bc3dd2f56970d06a
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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