Sodium hydride → 2-Hydroxymethyl-4-(4-mercaptobutylthio)-3-methylpyridine

HRID 342638

Reaktionsgleichung

Reaktionsgleichung von HRID 342638
[H-].[Na+].[CH2:3]([SH:8])[CH2:4][CH2:5][CH2:6][SH:7].Cl[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][OH:17])[C:11]=1[CH3:18]>CN(C=O)C.C(O)(=O)C>[OH:17][CH2:16][C:12]1[C:11]([CH3:18])=[C:10]([S:7][CH2:6][CH2:5][CH2:4][CH2:3][SH:8])[CH:15]=[CH:14][N:13]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 791481,4-ButanedithiolHCID 9817485(4-Chloro-3-methylpyridin-2-yl)methanol

Produkt 1

HCID 540725972-Hydroxymethyl-4-(4-mercaptobutylthio)-3-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

4.2 g (145 mmol) of sodium hydride (80% in paraffin) are initially introduced in 100 ml of DMF with ice-cooling. 35.5 g (290 mmol) of 1,4-butanedithiol are slowly added dropwise. After the evolution of gas has ended, 15.3 g (97 mmol) of 4-chloro-2-hydroxymethyl-3-methylpyridine in 20 ml of DMF are added drop-wise. After about 30 minutes, the mixture is allowed to come to RT and is stirred at this temperature for 12 h. It is diluted with 800 ml of ice-water and neutralized with acetic acid. The mixture is extracted 3 times with dichloromethane. The combined organic phases are washed 4 times with water, dried over magnesium sulfate, filtered and concentrated. The crude product is chromatographed on silica gel using ethyl acetate/conc. ammonia=99/1. The title compound is obtained as a yellow crystallizate. M.p. 58°-63° C.; yield 13 g (55% of theory).

Aufarbeitung

  1. temperaturecooling
  2. customto come to RT
  3. extractionThe mixture is extracted 3 times with dichloromethane
  4. washThe combined organic phases are washed 4 times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2367bd04bbdd4f5e832b60b402c47afd
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859030

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