Thionyl Chloride → 6-(Chloromethyl)-5-methyl-2-pyridinecarbonitrile

HRID 2356628Notes

Reaction equation

HRID 2356628 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[CH3:11].S(Cl)([Cl:14])=O>ClCCl>[Cl:14][CH2:2][C:3]1[N:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68458843HCID 68458843, compound

Product 1

HCID 552981476-(Chloromethyl)-5-methyl-2-pyridinecarbonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(hydroxymethyl)-5-methyl-2-pyridinecarbonitrile (184 mg) and thionyl chloride (0.16 ml) in dichloromethane (3.5 ml) was stirred at ambient temperature for 7 hours. Solvent was removed in vacuo and toluene (2 ml) added then removed in vacuo to afford the title compound (205 mg, 99%) as a pale buff solid.

Workup

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

Sources & evidence

ORD record
ord-ab1a1929872747a595afb436cc78c92e
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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