Triethylamine → 4-(4-Chlorobutylthio)pyridine

HRID 6190

Reaktionsgleichung

Reaktionsgleichung von HRID 6190
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][Cl:13].C(N(CC)CC)C>C(O)C>[Cl:13][CH2:12][CH2:11][CH2:10][CH2:9][S:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 813641-Bromo-4-chlorobutaneHCID 178418431pyridine-4-thiol

Produkt 1

HCID 158169784-(4-Chlorobutylthio)pyridineAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 33.35 g (0.30 mol) of 4-mercaptopyridine and 51.44 g (0.30 mol) of 1-bromo-4-chlorobutane in 500 ml of ethanol, 41.9 ml (0.30 mol) of triethylamine was added, and the mixture was stirred at room temperature for 5 hours. The solvent was distilled off and chloroform was added to the residue. The mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/n-hexane =1:1) to give 54.27 g of the desired compound (89.7% yield, colorless oil).

Aufarbeitung

  1. additionwas added
  2. distillationThe solvent was distilled off
  3. additionchloroform was added to the residue
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate/n-hexane =1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4aaaa3a6821445dabee298f6b50af2bd
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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