Cysteamine Hydrochloride → 2-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amine

HRID 1583408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583408
[OH-].[Na+].Cl.Cl[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.Cl.[SH:13][CH2:14][CH2:15][NH2:16]>C(O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][S:13][CH2:14][CH2:15][NH2:16])[CH:7]=1

Komponenten

5

Edukt 3

HCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochloride

Produkt 1

HCID 134987022-{[(Pyridin-3-yl)methyl]sulfanyl}ethan-1-amineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

16.8 g of sodium hydroxide was dissolved in 350 ml of ethanol and 17.2 g of 3-chloromethylpyridine hydrochloride and 23.7 g of 2-mercaptoethanamine hydrochloride were added with ice bath cooling. The reaction mixture was allowed to warm to room temperature over 2 hours, was concentrated, diluted with water, and extracted with 3×100 ml of dichloromethane. The combined organic layers were washed with saturated brine, dried over potassium carbonate and concentrated. The residue was distilled to give 12.30 g (70%) of 2-[[(3-pyridyl)methyl]thio]ethanamine, bp 115°-125° C./0.1 mm.

Aufarbeitung

  1. temperaturecooling
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. extractionextracted with 3×100 ml of dichloromethane
  5. washThe combined organic layers were washed with saturated brine
  6. dry with materialdried over potassium carbonate
  7. concentrationconcentrated
  8. distillationThe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-666bb7d55530477185b67764c524726a
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04551460

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