Hydrochloric Acid → 4-(3-Mercaptopyridin-4-yl)benzonitrile

HRID 470382

Reaktionsgleichung

Reaktionsgleichung von HRID 470382
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[S-2:16].[Na+].[Na+].Cl>CN(C=O)C>[SH:16][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14804Sodium SulfideHCID 108564354-(3-Fluoropyridin-4-yl)benzonitrile

Produkt 1

HCID 679970614-(3-Mercaptopyridin-4-yl)benzonitrileAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 4-(3-fluoropyridin-4-yl)benzonitrile (1.08 g, 5.4 mmol) and sodium sulfide (0.84 g, 10.8 mmol) in DMF (20 mL) was stirred at 130° C. for 0.5 hours. While the reaction was cooled in ice water bath, aqueous HCl (6N, 2.5 mL) was added drop wise with rigorous stirring. The resulting yellow paste was concentrated using rotary evaporation on a water bath (80° C.) to dryness. The resulting yellow solid was extracted with methanol (4×20 mL). The combined extracts were concentrated to dryness to give a yellow solid (1.1 g, 96%).

Aufarbeitung

  1. concentrationThe resulting yellow paste was concentrated
  2. customevaporation on a water bath (80° C.) to dryness
  3. extractionThe resulting yellow solid was extracted with methanol (4×20 mL)
  4. concentrationThe combined extracts were concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-cc55aeea824d4cfabb0fc277184748da
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629278B2

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