Thionyl Chloride → HCID 10827530, compound

HRID 1756636Notes

Reaction equation

HRID 1756636 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10516434HCID 10516434, compound

Product 1

HCID 10827530HCID 10827530, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-hydroxymethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine (9.4 g) in chloroform (100 ml) was added thionyl chloride (7.0 g) and the mixture was stirred under reflux for 30 minutes. After cooling, the reaction mixture was washed with saturated aqueous solution of sodium bicarbonate and then water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 5-chloromethyl-2-[2-(4-nitrophenoxy)ethyl]pyridine (9.7 g, yield: 85%). The compound was recrystallized from ethyl acetate-hexane to obtain colorless needles, m.p. 77°-78° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with saturated aqueous solution of sodium bicarbonate
  4. dry with materialwater, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6241de844d04acea0c19bfe4949718e
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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