Water → 2-{[3-(Hydroxymethyl)phenyl]sulfanyl}pyridine-4-carbonitrile

HRID 2266996

Reaktionsgleichung

Reaktionsgleichung von HRID 2266996
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([S:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])[CH:4]=1)#[N:2].[BH4-].[Na+].O>S(Cl)(Cl)=O.O1CCOCC1>[OH:14][CH2:13][C:12]1[CH:11]=[C:10]([S:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=2)[C:1]#[N:2])[CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 573554593-[(4-Cyanopyridin-2-YL)sulfanyl]benzoic acid

Produkt 1

HCID 573554602-{[3-(Hydroxymethyl)phenyl]sulfanyl}pyridine-4-carbonitrileAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24386Thionyl ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Dissolve 3-(4-cyano-pyridin-2-ylsulfanyl)-benzoic acid (920 mg, 3.59 mmol) in thionyl chloride (50 mL) and stir. Heat to reflux. After 2 hours, concentrate under reduced pressure to give a residue. Dissolve residue in dioxane (100 mL) and add sodium borohydride (1.36 g, 35.9 mmol). Heat to 50° C. After 2 hours, cool to ambient temperature and add water. Extract with ethyl acetate, combine organic layers, dry with sodium sulfate, filter and concentrate to give the title compound as a yellow oil (378 mg, 44%): 1H NMR (DMSO-d6) δ 4.56 (d, 2H), 5.31 (t, 1H), 7.38 (m, 1H), 7.48 (m, 3H), 7.55 (m, 1H), 7.59 (dd, 1H), 8.62 (dd, 1H).

Aufarbeitung

  1. temperatureHeat to reflux
  2. concentrationconcentrate under reduced pressure
  3. customto give a residue
  4. waitAfter 2 hours
  5. temperaturecool to ambient temperature
  6. extractionExtract with ethyl acetate
  7. dry with materialdry with sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-79edc97989794574a4b3cc5cd18ed6d2
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858646B2

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