Thionyl Chloride → 2-Chloromethyl-4-(3-methoxypropoxy)-3,5-dimethylpyridine

HRID 727923Notes

Reaction equation

HRID 727923 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]([CH3:16])=[CH:5][N:4]=1.S(Cl)([Cl:19])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:19][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]([CH3:16])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 151662294-(3-Methoxypropoxy)-3,5-dimethyl-2-pyridinemethanol

Product 1

HCID 151663232-Chloromethyl-4-(3-methoxypropoxy)-3,5-dimethylpyridineYield 88.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

4.70 g of crude 2-hydroxymethyl-4-(3-methoxypropoxy)-3,5-dimethylpyridine was dissolved in 50 ml of chloroform to obtain a solution. A solution of 2.7 g of thionyl chloride in 10 ml of chloroform was dropwise added to the above solution at 0° C. and the obtained mixture was stirred at 0° C. for one hour. After the completion of the reaction, the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and extracted with 150 ml of chloroform twice. The extract was dried over magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The obtained residue was dried in a vacuum to obtain 4.52 g of the title compound as a crude oil.

Workup

  1. customto obtain a solution
  2. customAfter the completion of the reaction
  3. extractionextracted with 150 ml of chloroform twice
  4. dry with materialThe extract was dried over magnesium sulfate
  5. filtrationfiltered
  6. distillationThe filtrate was distilled
  7. customto remove the solvent
  8. customThe obtained residue was dried in a vacuum

Sources & evidence

ORD record
ord-41ac267683f042c1bc62f85d2655f768
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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