Acetic Acid → Methyl pyrazine-2-carboximidate

HRID 327130Notes

Reaction equation

HRID 327130 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-9561216e82a74c3f847d6c58ac10e7e4
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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