Triethylamine → 4-[3-(4-n-Butylbenzoylamino)propylthio]pyridine hydrochloride

HRID 964082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 964082
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH2:21]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([Cl:31])=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[ClH:31].[CH2:21]([C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[O:30])=[CH:32][CH:33]=1)[CH2:22][CH2:23][CH3:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1200494-Butylbenzoyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Produkt 1

HCID 190790794-[3-(4-n-Butylbenzoylamino)propylthio]pyridine hydrochlorideAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.78 ml (19.9 mmol) of triethylamine in 40 ml of methylene chloride was added 0.93 ml (4.96 mmol) of 4-n-butylbenzoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minute. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.10 g of the desired compound (free base) (80.7%, colorless wax), mp: 46.0°-47.0° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minute
  3. washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1bcf64abe7b947029f099652c364da34
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767121

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