Acetic Acid → 3-Methoxy-2-pyrazinecarboxamide

HRID 1108447Notes

Reaction equation

HRID 1108447 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].C[O-].[Na+].[C:11]([OH:14])(=O)C.[CH:15]([CH:17]=O)=O>CO>[CH3:11][O:14][C:6]1[C:2]([C:3]([NH2:5])=[O:4])=[N:1][CH:15]=[CH:17][N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7860GlyoxalHCID 983412-Amino-2-cyanoacetamideHCID 10942334Sodium Methoxide

Product 1

HCID 125710393-Methoxy-2-pyrazinecarboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Under argon, 1 g (10.1 mmol) of 2-amino-2-cyanoacetamide was initially charged in 10 g of methanol. 0.25 g (1.4 mmol) of sodium methoxide solution (30%) was added and the mixture was stirred at 20° C. for 2 hours. After neutralization with 0.084 g (1.4 mmol) of acetic acid, 2.27 g (20 mmol) of glyoxal solution (40%) was added. The mixture was stirred at 20° C. for 2 hours and then at 50° C. for 2 hours. The solvent was distilled off. This gave 0.75 g of 3-methyoxypyrazine-2-carboxamide. The yield was 50 percent. Other data concerning the title product was:

Workup

  1. stirringThe mixture was stirred at 20° C. for 2 hours
  2. waitat 50° C. for 2 hours
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ac8457f7220d4f559da17fc46611ca90
Source dataset
uspto-grants-2000_05
Patent number
US06066736

Reaction notes

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