Sulfuric Acid → N-tert-butylpyrazine-2-carboxamide

HRID 582245

Reaktionsgleichung

Reaktionsgleichung von HRID 582245
S(=O)(=O)(O)O.[C:6]([C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)#[N:7].[C:14](O)([CH3:17])([CH3:16])[CH3:15].[OH-:19].[Na+]>O>[C:14]([NH:7][C:6]([C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)=[O:19])([CH3:17])([CH3:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 73172Pyrazinecarbonitrile

Produkt 1

HCID 4462842N-tert-butylpyrazine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 1030 g of an 80% aqueous solution of sulfuric acid (8.40 moles of sulfuric acid), 220.5 g (2.10 moles) of 2-cyanopyrazine was added dropwise keeping the internal temperature at 40° C. or less with stirring. In succession, 187 g (2.52 moles) of tert-butyl alcohol was added dropwise to the mixture, keeping the internal temperature at 9° to 15° C., over 3 hours. Further, the temperature was kept at the same temperature for 2.5 hours. After the reaction, the reaction liquid was added to 3500 g of water with stirring. Thus obtained mixture was neutralized with an aqueous solution of sodium hydroxide. Precipitated crystalline solid was separated by filtration, washed with water and then dried to obtain 338.7 g (1.89 moles) of N-tert-butyl-2-pyrazine-carboxamide. It had a melting point of 88° to 90° C. Further, from the water layer, from which the intended product had been separated by filtration, 7.17 g (0.04 mole) of the intended product was further obtained by extraction thereof with toluene. Therefore, the yield of N-tert-butyl-2-pyrazinecarboxamide obtained here was 91.9%.

Aufarbeitung

  1. customat 40° C. or less
  2. customat 9° to 15° C.
  3. waitFurther, the temperature was kept at the same temperature for 2.5 hours
  4. customAfter the reaction
  5. customthe reaction liquid
  6. stirringwith stirring
  7. customPrecipitated crystalline solid was separated by filtration
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9fdadf8460a44268ad330e47232344a9
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922873

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