Water → 4-Methylpyridine-2-sulfonyl fluoride

HRID 869742

Reaktionsgleichung

Reaktionsgleichung von HRID 869742
C([S:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1.[OH2:16].ClN1C(=[O:23])CCC1=O.[F-:25].[K+]>C(O)(=O)C>[CH3:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([S:8]([F:25])(=[O:23])=[O:16])[CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 522689Potassium FluorideHCID 583498362-(Benzylthio)-4-methylpyridine

Produkt 1

HCID 583498404-Methylpyridine-2-sulfonyl fluoride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-(benzylsulfanyl)-4-methylpyridine (1.40 g) in acetic acid (10 mL)-water (5 mL) was added N-chlorosuccinimide (3.48 g) under ice-cooling, and the mixture was gradually warmed to room temperature and stirred for 4 hr. Potassium fluoride (379 mg) was added at room temperature and the mixture was stirred for 18 hr. The reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate solution. The separated aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1→11:1) to give the title compound as a crude pale-yellow oil (yield 343 mg, 30%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 18 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. extractionThe separated aqueous layer was extracted with ethyl acetate
  7. washCombined organic layers were washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1→11:1)

Quellen und Nachweise

ORD-Eintrag
ord-21320a444ac44e8ca2128b0ad27bb47d
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969387B2

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