Phenylglyoxal → HCID 21702990, compound

HRID 1596738Notes

Reaction equation

HRID 1596738 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].[CH3:8][O-:9].[Na+].[C:11]1([C:17]([CH:19]=O)=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[CH3:8][O:9][C:6]1[C:2]([C:3]([NH2:5])=[O:4])=[N:1][CH:19]=[C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14090PhenylglyoxalHCID 983412-Amino-2-cyanoacetamideHCID 10942334Sodium Methoxide

Product 1

HCID 21702990HCID 21702990, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Under argon, 2 g (20 mmol) of 2-amino-2-cyanoacetamide was initially charged in 15 g of methanol. 0.55 g (3 mmol) of sodium methoxide solution (30%) was added and the mixture was stirred at 20° C. for 2 hours. At 0° C., 3.2 g (21 mmol) of phenylglyoxal was added and the mixture was then stirred at 0° C. for 2 hours and concentrated. The product was purified by column chromatography (eluent ethyl acetate/methanol 4/1). This gave 3 g of 3-methoxy-5-phenylpyrazine-2-carboxamide. The yield was 65 percent. Other data concerning the title product was:

Workup

  1. stirringthe mixture was then stirred at 0° C. for 2 hours
  2. concentrationconcentrated
  3. customThe product was purified by column chromatography (eluent ethyl acetate/methanol 4/1)

Sources & evidence

ORD record
ord-f31e1e189f014dd9a56d5a3a03bda868
Source dataset
uspto-grants-2001_09
Patent number
US06291674B1

Reaction notes

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