Thionyl Chloride → HCID 22625098, compound

HRID 1384637Notes

Reaction equation

HRID 1384637 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1>ClC(Cl)Cl>[ClH:3].[Cl:3][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21936007HCID 21936007, compound

Product 1

HCID 22625098HCID 22625098, compoundYield 122.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
5 °C

Procedure

Thionyl chloride (2.2 ml, 30 mmol) was added slowly to a solution of 4-(3-hydroxypropoxy)pyridine (3.1 g, 20 mmol) in trichloromethane (40 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-(3-chloropropoxy)pyridine hydrochloride (3.81 g, 91%) as a solid. 1H NMR Spectrum: (DMSOd6) 2.22(m, 2H); 3.80(t, 2H); 4.42(t, 2H); 7.55(d, 2H); 8.72(d, 2H) MS-ESI: 172 [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-31e7bbe5f76c43c38b74c51e3332bd98
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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