Acetic Acid → Methyl 3-methoxy-5-methylpyrazine-2-carboxylate

HRID 1978140

Reaktionsgleichung

Reaktionsgleichung von HRID 1978140
[NH2:1][CH:2]([C:5]#[N:6])[C:3]#N.[C:7]1([CH3:17])C=CC(S([O-])(=O)=O)=C[CH:8]=1.C[O-:19].[Na+].[C:21]([OH:24])(=O)C.C[C:26](C=O)=[O:27].Cl>CO>[CH3:26][O:27][C:8]1[C:7]([C:17]([O:24][CH3:21])=[O:19])=[N:6][CH:5]=[C:2]([CH3:3])[N:1]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 880MethylglyoxalHCID 10942334Sodium MethoxideHCID 187969712-Aminomalononitrile 4-toluenesulfonate

Produkt 1

HCID 21702987Methyl 3-methoxy-5-methylpyrazine-2-carboxylateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

Under argon, 5 g (19.3 mmol) of 2-aminomalononitrile-4-toluenesulfonate was initially charged in 50 g of methanol. 4.09 g (22.7 mmol) of sodium methoxide solution (30%) was added and the mixture was stirred at 2° C. for 2 hours. After neutralization with 0.204 g (3.4 mmol) of acetic acid, 3.6 g (19.9 mmol) of methylglyoxal solution (40%) was added. The mixture was stirred at 40° C. for 2 hours and then, at 20° C., 9.2 g (80 mmol) of hydrochloric acid (32%) was added and the mixture was stirred at 20° C. for 6 hours. The solvent was distilled off and the methyl 3-methoxy-5-methylpyrazine-2-carboxylate was extracted with methylene chloride. This gave 1 g of methyl 3-methoxy-5-methylpyrazine-2-carboxylate. The yield was 27 percent Other data concerning the title product was:

Aufarbeitung

  1. stirringThe mixture was stirred at 40° C. for 2 hours
  2. stirringthe mixture was stirred at 20° C. for 6 hours
  3. distillationThe solvent was distilled off
  4. extractionthe methyl 3-methoxy-5-methylpyrazine-2-carboxylate was extracted with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-51fd19501f9b403d87cd1b28889fd240
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235905B1

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