2,5-Dimethylpyrazine → 2-(Chloromethyl)-5-methylpyrazine

HRID 2200605Notes

Reaction equation

HRID 2200605 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C(=O)N([Cl:16])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:16][CH2:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 312522,5-DimethylpyrazineHCID 31398Chlorosuccinimide

Product 1

HCID 132210252-(Chloromethyl)-5-methylpyrazineYield 20.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,5-dimethylpyrazine (500 mg, 4.62 mmol) in carbon tetrachloride (7 mL) was added NCS (679 mg, 5.09 mmol) followed by BPO (20 mg) and the mixture was heated to 80° C. for 6 hours. The mixture was diluted with DCM and extracted with saturated aqueous sodium sulfite solution and brine. The organic layer was dried and concentrated to give a crude product which was purified via silica gel chromatography eluting with petroleum ether/ethyl acetate (1:0 to 15:1) to give 2-(chloromethyl)-5-methylpyrazine (133 mg, 20.19% yield) as yellow oil. LCMS retention time 0.557 min; LCMS MH+ 143.

Workup

  1. extractionextracted with saturated aqueous sodium sulfite solution and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified via silica gel chromatography
  6. washeluting with petroleum ether/ethyl acetate (1:0 to 15:1)

Sources & evidence

ORD record
ord-01e4f8a247cd41bb91a1591d0ee25b5c
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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