Thionyl Chloride → 2-Chloromethyl-4-(3-methoxypropoxy)pyridine

HRID 727918Notes

Reaction equation

HRID 727918 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH:10]=[CH:9][N:8]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 151662262-Hydroxymethyl-4-(3-methoxypropoxy)pyridine

Product 1

HCID 151662252-Chloromethyl-4-(3-methoxypropoxy)pyridineYield 83.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2.60 g (0.022 mol) of thionyl chloride in 10 ml of chloroform was dropwise added to a solution of 3.64 g (0.018 mol) of 2-hydroxymethyl-4-methoxypropoxypyridine in 60 ml of chloroform under cooling with ice. The obtained mixture was stirred for one hour, neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform. The chloroform layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure to obtain 3.23 g of the title compound as a crude product.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-ed3050b8351c4cb2bc4a92733aac9252
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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