Thiophenol → 2-[(Phenylsulfanyl)methyl]pyridine--hydrogen chloride (1/1)

HRID 1156763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156763
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Cl.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][Cl:17]>C(O)C>[ClH:17].[C:1]1([S:7][CH2:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 23392Picolyl chloride hydrochlorideHCID 5360545Sodium

Produkt 1

HCID 124744352-[(Phenylsulfanyl)methyl]pyridine--hydrogen chloride (1/1)Ausbeute 5,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Thiophenol (21 ml) was added to a solution of sodium (4.6 g) in ethanol (100 ml). To the resulting solution was added 2-picolyl chloride, hydrochloride (15 g) and the mixture was heated at reflux for 2 hours. Precipitated sodium chloride was removed by filtration and the solution was acidified with ethereal HCl. The solvent was removed by evaporation and the residue induced to crystallise by trituration with ether. Recrystallisation from ethanol-ether gave 2-((phenylthio)methyl)pyridine, hydrochloride (5.0 g) mp 142°-4° C. (Found: C, 60.6; H, 5.25; N, 5.5. C12H11NS, HCl requires C, 60.6; H, 5.1; N, 5.9%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customPrecipitated sodium chloride was removed by filtration
  4. customThe solvent was removed by evaporation
  5. customthe residue induced to crystallise by trituration with ether
  6. customRecrystallisation from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-ed4f0ec217ab461c92c10a6121a781c1
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04337259

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