Water → 1,2-bis[N-[4-(4-pyridylthio)butyl]-N-propionylamino]benzene

HRID 274728

Reaktionsgleichung

Reaktionsgleichung von HRID 274728
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30]Cl)[C:16](=[O:19])[CH2:17][CH3:18].O>CS(C)=O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]([C:32](=[O:35])[CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH2:30][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:16](=[O:19])[CH2:17][CH3:18])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 190792541,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzeneHCID 178418431pyridine-4-thiol

Produkt 1

HCID 190791281,2-bis[N-[4-(4-pyridylthio)butyl]-N-propionylamino]benzeneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 525 mg (4.7 mmol) of 4-mercaptopyridine and 265 mg (4.7 mmol) of potassium hydroxide in 20 ml of dimethyl sulfoxide, 760 mg (1.89 mmol) of 1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene was added at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate to ethyl acetate/ethanol=20:1 to 10:1 to 5:1) to give 0.84 g of the desired product (81.0% yield, pale yellow crystals).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by column chromatography (eluent: ethyl acetate to ethyl acetate/ethanol=20:1 to 10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b69c4398ddb40cc9bd6cbaa18c6d08a
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389658

Verknüpfte Notizen

Wird geladen…