Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine hydrochloride

HRID 1620802Notes

Reaction equation

HRID 1620802 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>ClCCl>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12325387(5-Methylpyridin-2-yl)methanol

Product 1

HCID 233137952-(Chloromethyl)-5-methylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-methyl-pyridin-2-yl)-methanol (310 g) in dichloromethane (1.2 L) was added thionyl chloride (200 mL) dropwise over 1.5 hours. The reaction was stirred for 2 hours, and then concentrated under vacuum. Ethyl acetate (1 L) was added, and the mixture was again concentrated to dryness. Additional ethyl acetate (1.5 L) was added, and the suspension was stirred for 30 minutes and then filtered to isolate the desired product as a solid, which was dried under nitrogen.

Workup

  1. concentrationconcentrated under vacuum
  2. additionEthyl acetate (1 L) was added
  3. concentrationthe mixture was again concentrated to dryness
  4. additionAdditional ethyl acetate (1.5 L) was added
  5. stirringthe suspension was stirred for 30 minutes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c449a2c60b044e779855531c750b451a
Source dataset
uspto-grants-2014_07
Patent number
US08772495B2

Reaction notes

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