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

HRID 1074922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074922
[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)

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)methylpyridine, 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-d55359f65cf946abb94274934af0d1d5
Quelldatensatz
uspto-grants-1983_07
Patentnummer
US04394509

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