Benzoyl Peroxide → 2-(Bromomethyl)-3,5,6-trimethylpyrazine

HRID 633774Notes

Reaction equation

HRID 633774 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[N:4][C:3]=1[CH3:10].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:3]1[C:2]([CH3:1])=[N:7][C:6]([CH3:8])=[C:5]([CH3:9])[N:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 14296Tetramethylpyrazine3×HCID 67184N-bromobutanimide2×

Product 1

HCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

More preferably, dehydrated tetramethylpyrazine is dissolved into an organic solvent, preferably CCl4, and then NBS is added at a mole ratio of tetramethylpyrazine to NBS=1:0.7. Then a small amount of benzoylperoxide is added as the radical initiator. The reaction is carried out under the illumination of an incandescent lamp and the reaction liquid is refluxed to react for 10-12 h. Next the reaction liquid is cooled and condensed, and the excess tetramethylpyrazine is sucked away under reduced pressure in 60-70° C. water bath. The residue is kept in a fridge for standing, and 2-bromomethyl-3,5,6-trimethyl pyrazine is obtained as a pale-red half-oily substance.

Workup

  1. customThe reaction is carried out under the illumination of an incandescent lamp
  2. customthe reaction liquid
  3. temperatureis refluxed
  4. customto react for 10-12 h
  5. customNext the reaction liquid
  6. temperatureis cooled
  7. customcondensed
  8. customis sucked away under reduced pressure in 60-70° C.

Sources & evidence

ORD record
ord-4c994169615342248c52676934988c64
Source dataset
uspto-grants-2016_04
Patent number
US09321804B2

Reaction notes

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