Benzoyl chloride → 4-[4-(Benzoylamino)butylthio]pyridine

HRID 964138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964138
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 135575374-[(Pyridin-4-yl)sulfanyl]butan-1-amine

Produkt 1

HCID 190791704-[4-(Benzoylamino)butylthio]pyridineAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 100 g (5.49 mmol) of 4-(4-aminobutylthio)pyridine and 0.92 ml (6.60 mmol) of triethylamine in 30 ml of methylene chloride, 0.67 ml (5.77 mmol) of benzoyl chloride was added with stirring under ice-cooling and the mixture was stirred at room temperature for 13 hours. The mixture was washed with saturated aqueous sodium bicarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.54 g of the desired compound (34.4% yield, colorless crystals), mp. 75°-77° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 13 hours
  3. washThe mixture was washed with saturated aqueous sodium bicarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0fc762c5567947859fab1a894a18f11c
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767121

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