Chloroform → Methyl 3-chloromethylpyrazine-2-carboxylate

HRID 2388627Notes

Reaction equation

HRID 2388627 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)[Cl:31]>>[Cl:31][CH2:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 7187Benzoyl PeroxideHCID 13153469Methyl 3-methylpyrazine-2-carboxylate

Product 1

HCID 67039637Methyl 3-chloromethylpyrazine-2-carboxylateYield 52%

Procedure

Methyl 3-methylpyrazine-2-carboxylate (2.44 g, 16 mmol) was dissolved in chloroform (100 ml) and N-chlorosuccinimde (2.14 g, 16 mmol) was added thereto. Then, benzoyl peroxide (110 mg, 70%, 0.32 mmol) was added and refluxed under heating for 30 hours. The reaction solution was cooled, followed by removing undissolved substance by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by using silica gel chromatography (hexane:ethyl acetate=1:1)to obtain 1.55 g of the desired compound.

Workup

  1. additionN-chlorosuccinimde (2.14 g, 16 mmol) was added
  2. temperaturerefluxed
  3. temperatureunder heating for 30 hours
  4. temperatureThe reaction solution was cooled
  5. customby removing undissolved substance
  6. filtrationby filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified

Sources & evidence

ORD record
ord-198b8725c6e9480185ee526fccd7eabb
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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