Sulfuric Acid → 3-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide

HRID 534058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534058
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:12]([O:13][C:14]2[C:15]([C:27]#[N:28])=[N:16][CH:17]=[C:18]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:19]=2)=[C:11]([CH3:29])[CH:10]=[CH:9][N:8]=1.[OH-:30].[Na+]>>[CH3:6][C:7]1[C:12]([O:13][C:14]2[C:15]([C:27]([NH2:28])=[O:30])=[N:16][CH:17]=[C:18]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH:19]=2)=[C:11]([CH3:29])[CH:10]=[CH:9][N:8]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674858013-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile

Produkt 1

HCID 674862983-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamideAusbeute 94,4 %

Versuchsvorschrift

Concentrated sulfuric acid (8 mL) was added to 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (2.03 g, 6.07 mmol). The reaction was stirred overnight, then poured onto ice (100 g), cooled in an ice bath and made basic to pH 10 with 50% NaOH. The reaction was extracted with ethyl acetate, washed with brine, dried (MgSO4), and concentrated to afford 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinamide (2.02 g, 5.73 mmol, 94.4% yield) as a white solid.

Aufarbeitung

  1. additionpoured onto ice (100 g)
  2. temperaturecooled in an ice bath
  3. extractionThe reaction was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1a911116c75c44cf8aa7d85914bf52a3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853409B2

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