Pyridine → N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamide

HRID 127930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127930
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14]O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][Cl:24])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 23470789HCID 23470789, Verbindung

Produkt 1

HCID 14005891N-{4-[(3-Chloropropyl)sulfanyl]phenyl}acetamideAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of 5.62 g (0.025 mole) of 3-(4'-acetamidophenylthio)propanol in 25 ml of methylene chloride and 2.03 ml of pyridine (0.025 mole) is added 3.7 g of thionyl chloride (0.031 mole) in 10 ml of methylene chloride. After the exothermic reaction subsides, the mixture is heated at reflux for 0.5 hr. The reaction mixture is poured into 100 ml of ice-water with stirring. The organic layer is separated, dried and concentrated to a dark red solid. Extraction of the latter with ether in a Soxlet apparatus yields 3.5 g of 3-(p-acetamidophenylthio)propyl chloride having the correct IR and NMR spectra.

Aufarbeitung

  1. customAfter the exothermic reaction subsides
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 0.5 hr
  4. customThe organic layer is separated
  5. customdried
  6. concentrationconcentrated to a dark red solid
  7. extractionExtraction of the latter with ether in a Soxlet apparatus

Quellen und Nachweise

ORD-Eintrag
ord-24d1c014e33942fbb9b03058e30bb6e4
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258045

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