Sulfuric Acid → 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide

HRID 1523668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523668
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:19]S(O)(=O)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]([NH2:9])=[O:19])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674868715-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

Produkt 1

HCID 674864005-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A flask was charged with 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (7.0 g, 23 mmol) and H2SO4 (56 g, 570 mmol) and the reaction was stirred at ambient temperature overnight. The reaction was cooled in an ice bath and water (100 mL) was carefully added. 40% NaOH solution was slowly added till the pH was about 12. The mixture was extracted with ethyl acetate and dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide (7.4 g, 23 mmol, 100% yield) as light yellow solid.

Aufarbeitung

  1. temperatureThe reaction was cooled in an ice bath
  2. extractionThe mixture was extracted with ethyl acetate and dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9988782e8804c618b38fdc4891863b6
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079890B2

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