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

HRID 45774

Reaktionsgleichung

Reaktionsgleichung von HRID 45774
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-dfe61e8317574b2dbb0f1e3faa3d24a2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541589B2

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