Carbon Tetrachloride → 2,3-Bis(chloromethyl)pyrazine

HRID 1835274Notes

Reaction equation

HRID 1835274 reaction equation
[CH3:1][C:2]1[C:7](C)=[N:6][CH:5]=[CH:4][N:3]=1.[Cl:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N1C=CN=CC=1.[C:41]([Cl:45])(Cl)(Cl)Cl>>[Cl:9][CH2:1][C:2]1[C:7]([CH2:41][Cl:45])=[N:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 5

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2×HCID 9261PyrazineHCID 222012,3-DimethylpyrazineHCID 31398Chlorosuccinimide

Product 1

HCID 132210262,3-Bis(chloromethyl)pyrazineYield 11%

Procedure

To a solution of 2,3-dimethylpyrazine (6.27 g, 57.4 mmol) in 100 mL of carbon tetrachloride was added N-chlorosuccinimide (16.7 g) followed by benzoyl peroxide (278 mg, 2 mol %) and the solution was heated to reflux for 16 h. The reaction was cooled, more benzoyl peroxide (278 mg, 2 mol %) was added and the reaction was refluxed for 5 h. The reaction was monitored by TLC until the disappearance of starting pyrazine. The reaction flask was cooled in an ice bath, the solution filtered, and the eluent was concentrated and chromatographed on SiO2 using 15% EtOAc in hexane. Obtained 1.14 g of the product (11% yield). MS found: (M+H)+=178.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction was cooled
  4. temperaturethe reaction was refluxed for 5 h
  5. temperatureThe reaction flask was cooled in an ice bath
  6. filtrationthe solution filtered
  7. concentrationthe eluent was concentrated
  8. customchromatographed on SiO2 using 15% EtOAc in hexane

Sources & evidence

ORD record
ord-632abc17d91646f09ca7ab83198ee29a
Source dataset
uspto-grants-2004_08
Patent number
US06770647B2

Reaction notes

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