Acetic Acid → Methyl pyrazine-2-carboximidate

HRID 1588559Notes

Reaction equation

HRID 1588559 reaction equation
[C:1]([C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1)#[N:2].[C:9](O)(=[O:11])C>CO.C[O-].[Na+]>[N:4]1[CH:5]=[CH:6][N:7]=[CH:8][C:3]=1[C:1](=[NH:2])[O:11][CH3:9]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 73172Pyrazinecarbonitrile

Product 1

HCID 470894Methyl pyrazine-2-carboximidateYield 910.8%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

Cyanopyrazine (5.26 g, 50 mmol) was dissolved in methanol (40 ml), and sodium methoxide (0.27 g, 5.0 mmol) was added. The reaction mixture was stirred at room temperature for 45 minutes. After the reaction was completed, acetic acid (0.33 g, 5.5 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Dichloromethane (50 ml) and diethyl ether (50 ml) were added to the concentrated residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl pyrazinecarboximidate (6.87 g) as colorless powder.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionDichloromethane (50 ml) and diethyl ether (50 ml) were added to the concentrated residue, and insolubles
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d90118962885413288235187c8ab366d
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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