Thionyl Chloride → 6-(Chloromethyl)-3-methyl-2-pyridinecarbonitrile

HRID 2356634Notes

Reaction equation

HRID 2356634 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[C:6]([CH3:11])=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O>ClCCl>[Cl:14][CH2:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[C:6]([CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 573366546-(Hydroxymethyl)-3-methylpyridine-2-carbonitrile

Product 1

HCID 552981486-(Chloromethyl)-3-methyl-2-pyridinecarbonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(Hydroxymethyl)-3-methyl-2-pyridinecarbonitrile (148 mg) and thionyl chloride (0.16 ml) in dichloromethane (3.5 ml) was stirred at ambient temperature for 6 hours. Solvent was removed in vacuo and toluene (2 ml) added then removed in vacuo to afford the title compound (160 mg, 96%) as a pale grey-green solid.

Workup

  1. customSolvent was removed in vacuo and toluene (2 ml)
  2. additionadded
  3. customthen removed in vacuo

Sources & evidence

ORD record
ord-9c45a851135140aab3b1fd1993edab01
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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