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

HRID 357572Notes

Reaction equation

HRID 357572 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. 1H-NMR (CDCl3) δ; 1.80~2.20 (m, 2H), 3.31 (s, 3H), 3.49 ((t, J=6.2 Hz, 2H), 4.07 (t, J=6.2 Hz, 2H), 4.55 (s, 2H), 6.52~6.96 (m, 2H), 8.26 (d, J=5.3 Hz, 1H)

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-ffe84c7e8fc340fca2e883609c2bf625
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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