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

HRID 1511076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511076
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 batch 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)picolinoamide (2.02 g, 5.73 mmol, 94.4% yield) as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2e97c7f2deb04242a97f8e4129df5899
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212045B2

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