1,3-Propanedithiol → [4-(3-Mercaptopropylsulfanyl)-3-methylpyridin-2-yl]methanol

HRID 1637614

Reaktionsgleichung

Reaktionsgleichung von HRID 1637614
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([SH:11])[CH2:8][CH2:9][SH:10].Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]>O>[SH:10][CH2:9][CH2:8][CH2:7][S:11][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]

Komponenten

5

Edukt 3

HCID 80131,3-PropanedithiolHCID 11430Potassium CarbonateHCID 16095907152402-96-5

Produkt 1

HCID 18404145[4-(3-Mercaptopropylsulfanyl)-3-methylpyridin-2-yl]methanolAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of potassium carbonate (691 g, 5 mol) in 1.5 l of water is treated with 1,3-propanedithiol (432.8 g, 4 mol) under a nitrogen atmosphere and heated to 80° C. A solution of (4-chloro-3-methylpyridin-2-yl)methanol hydrochloride (194.1 g, 1 mol) in 400 ml of water is then added dropwise at this temperature with vigorous stirring during the course of about 2 h. The mixture is additionally stirred at 80 to 85° C. for 18 h and then cooled to room temperature. After separating off the aqueous phase, the organic phase is treated with toluene (1.5 l) and washed with water (2×1 l). The organic phase is then extracted with 2M hydrochloric acid (2 l). The hydrochloric acid phase is concentrated and the residue is recrystallized from isopropanol. 159 g (60%) of the title compound are isolated. The crude product is employed without further purification for the synthesis of the compound of Example 1.

Aufarbeitung

  1. stirringThe mixture is additionally stirred at 80 to 85° C. for 18 h
  2. temperaturecooled to room temperature
  3. customAfter separating off the aqueous phase
  4. additionthe organic phase is treated with toluene (1.5 l)
  5. washwashed with water (2×1 l)
  6. extractionThe organic phase is then extracted with 2M hydrochloric acid (2 l)
  7. concentrationThe hydrochloric acid phase is concentrated
  8. customthe residue is recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-ec4eb38a64b045939f884a1987e9437b
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043242

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