Benzoyl chloride → 4-[3-(N-2-pyridylmethyl-N-benzoylamino)propylthio]pyridine

HRID 6137

Reaktionsgleichung

Reaktionsgleichung von HRID 6137
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 190791764-(3-(N-2-pyridylmethylamino)propylthio]pyridine

Produkt 1

HCID 190791504-[3-(N-2-pyridylmethyl-N-benzoylamino)propylthio]pyridineAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.60 g (6.17 mmol) of 4-[3-(N-2-pyridylmethylamino)propylthio)pyridine and 1.05 ml (7.40 mmol) of triethylamine in 10 ml of methylene chloride, 0.86 ml (7.40 mmol) of benzoyl 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/methanol=10:1) to obtain 1.32 g of the desired compound (yield: 58.9%, yellow oil).

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/methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f6517c3bd51c417b92bd4b78dfc8e915
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246948

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