Sodium hydride → 2-Sulfanylpyridine-3-carbonitrile

HRID 502593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502593
[C:1]([C:3]1[C:4]([S:9]CCC(OC)=O)=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+]>O1CCCC1>[S:9]=[C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][NH:5]1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 13793439Methyl 3-(3-cyanopyridin-2-ylthio)propanoate

Produkt 1

HCID 43864192-Sulfanylpyridine-3-carbonitrileAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-(3-cyanopyridin-2-ylthio)propanoate (1.5 g, 6.8 mmol), sodium hydride (0.36 g, 15 mmol) and tetrahydrofuran (30 ml) was heated at reflux for 5 h. The reaction was quenched by the addition of ethanol (5 ml). The solvents removed under reduced pressure and the residue was treated with water (50 ml). The ph was adjusted to 6 and the mixture was filtered to yield 2-thioxo-1,2-dihydropyridine-3-carbonitrile (0.64 g). An analytically pure sample was prepared by recrystallisation from ethanol, yellow needles, mp 243-246° C. (lit. mp 248-250° C.). 1H NMR (DMSO-d6): 14.30 (br s, exchangeable, 1H), 8.12 (dd, 1H), 7.94 (dd, 1H), 6.86 ppm (dd, 1H). MW=136 confirmed by LC-MS, tr=5.27 min (Method C) MH+=137.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customThe reaction was quenched by the addition of ethanol (5 ml)
  4. customThe solvents removed under reduced pressure
  5. additionthe residue was treated with water (50 ml)
  6. filtrationthe mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-f8880c6a240b43f7a8d804ed1004abe5
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776847B2

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