Triethylamine → 3-[3-(Thenoylamino)propylthio]pyridine

HRID 6118

Reaktionsgleichung

Reaktionsgleichung von HRID 6118
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C.[C:21]1([C:26](Cl)=[O:27])[S:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:21]1([C:26]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:27])[S:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 190791133-(3-Aminopropylthio)pyridine dihydrochloride

Produkt 1

HCID 190791443-[3-(Thenoylamino)propylthio]pyridineAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2.00 g (8.29 mmol) of 3-(3-aminopropylthio)pyridine dihydrochloride and 4.16 ml (29.9 mmol) of triethylamine in 80 ml of methylene chloride, 1.06 ml (9.95 mmol) of 2-thenoyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain powder. The powder was washed with ether and dried to obtain 1.97 g of the desired compound (yield: 85.3%, yellow powder).

Aufarbeitung

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  4. customdried
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)
  7. customto obtain powder
  8. washThe powder was washed with ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a90ae34ce8714ddbad0eb996ca1db373
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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