Thionyl Chloride → 2-Chloromethyl-4-(4-methoxybutoxy)pyridine

HRID 609850Notes

Reaction equation

HRID 609850 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:18])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:18][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 151662242-Hydroxymethyl-4-(4-methoxybutoxy)pyridine

Product 1

HCID 151662232-Chloromethyl-4-(4-methoxybutoxy)pyridineYield 83.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

5.6 g of crude 2-hydroxymethyl-4(4-methoxybutoxy)pyridine was dissolved in 80 ml of chloroform to obtain a solution. A solution of 3.8 g of thionyl chloride in 10 ml of chloroform was dropwise added to this solution at 0° C. 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 200 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 5.09 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 200 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-bda5f107551b44808eaf383623be8c0c
Source dataset
uspto-grants-1999_12
Patent number
US05998445

Reaction notes

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