Sulfuric Acid → HCID 67486463, Verbindung

HRID 534051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534051
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:8]([S:13][C:14]2[CH:15]=[C:16]([O:22][C:23]3[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]([C:20]#[N:21])=[N:18][CH:19]=2)=[N:9][CH:10]=[CH:11][CH:12]=1.[OH-:30].[Na+]>>[CH3:6][C:7]1[C:8]([S:13][C:14]2[CH:15]=[C:16]([O:22][C:23]3[C:24]([CH3:29])=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]([C:20]([NH2:21])=[O:30])=[N:18][CH:19]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67487618HCID 67487618, Verbindung

Produkt 1

HCID 67486463HCID 67486463, VerbindungAusbeute 94,9 %

Versuchsvorschrift

Concentrated sulfuric acid (8 mL) was added to 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinonitrile (1.40 g, 4.19 mmol). The reaction was stirred over the weekend, then poured onto ice (100 g), cooled in an ice bath and made basic to pH 10 with 50% NaOH. The reaction mixture was extracted with ethyl acetate, washed with brine, dried (MgSO4), and concentrated to afford 5-(3-methylpyridin-2-ylthio)-3-(2-methylpyridin-3-yloxy)picolinamide (1.40 g, 3.97 mmol, 94.9% yield) as a colorless oil which became a white crystalline solid overnight under vacuo.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d38ae19e5e3d4144b0b5f2b51ef34969
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853409B2

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