N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamide → Thionicotinamide

HRID 404760

Reaktionsgleichung

Reaktionsgleichung von HRID 404760
FC1C=CC([N:8](CC2C=CC=CN=2)[C:9](=O)[C:10]2[CH:15]=[CH:14][C:13](Cl)=[N:12][CH:11]=2)=CC=1.[SH2:25].[Na]>CN(C)C=O.C(OCC)(=O)C>[C:9]([NH2:8])(=[S:25])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1

Komponenten

5

Edukt 2

HCID 59446415N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamideHCID 86586439Sodium hydrogen sulphide

Produkt 1

HCID 737155ThionicotinamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a round bottom flask, N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamide intermediate X (1.078 g, 3.16 mmol) and anhydrous sodium hydrogen sulfide (0.354 g, 6.32 mmol) was suspended in anhydrous dimethylformamide (10 mL). The suspension was heated to reflux, and the reaction mixture turned a deep green color. After 1 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (20 mL). The aqueous layer was back extracted with ethyl acetate (2×20 ml), and the organic layers combined and washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and evaporated by rotary evaporation to yield 0.88 g (82%) of thionicotinamide intermediate XI as a dark yellow oil. TLC (EtOAc/hexanes, 2:1) Rf=0.1; ESI-MS m/z=339.9 [M+H]+.

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. washwashed with water (20 mL)
  4. extractionThe aqueous layer was back extracted with ethyl acetate (2×20 ml)
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-afd7bf82aaee4c1693024db9f017b9ce
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748623B2

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