Triethylamine → 4-[3-(1-Naphthoylamino)propylthio]pyridine hydrochloride

HRID 274644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274644
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.[C:21]1([C:31]([Cl:33])=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[ClH:33].[C:21]1([C:31]([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:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 701461-Naphthalenecarbonyl chlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Produkt 1

HCID 190792034-[3-(1-Naphthoylamino)propylthio]pyridine hydrochlorideAusbeute 74,8 %

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 trietylamine in 40 ml of methylene chloride was added 0.75 ml (4.98 mmol) of 1-naphthoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture 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: methanol/ethyl acetate=1:10) to obtain the powder which was washed with ether and dried to obtain 1.00 g of the desired compound (free base) (74.8%, yellow powder), mp: 113.0°-114.0° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washThe reaction mixture 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: methanol/ethyl acetate=1:10)
  7. customto obtain the powder which
  8. washwas washed with ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2326d2e8defd4e4db5409b84057d2bb5
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389658

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