Thionyl Chloride → HCID 22624879, compound

HRID 1384641Notes

Reaction equation

HRID 1384641 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22624967HCID 22624967, compound

Product 1

HCID 22624879HCID 22624879, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (0.98 ml, 13.5 mmol) was added slowly to a solution of 4-(2-hydroxyethylthio)pyridine (1.39 g, 9.0 mmol) in trichloromethane (25 ml) at 5° C. The mixture was stirred at 5° C. for 1 hour and then at ambient temperature for 2 hours. The volatiles were removed by evaporation, the residue azeotroped with toluene and dried under vacuum to give 4-(2-chloroethylthio)pyridine hydrochloride (500 mg, 26%) as a solid. 1H NMR Spectrum: (DMSOd6) 3.65(t, 2H); 3.90(t, 2H); 7.90(d, 2H); 8.60(d, 2H) MS-ESI: 174 [MH]+

Workup

  1. waitat ambient temperature for 2 hours
  2. customThe volatiles were removed by evaporation
  3. customthe residue azeotroped with toluene
  4. customdried under vacuum

Sources & evidence

ORD record
ord-864d36b629a5494cb14f2acfe1c971c5
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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