Thionyl Chloride → 4-(Chloromethyl)pyridine-2-carbonitrile

HRID 2202591Notes

Reaction equation

HRID 2202591 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:13][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]#[N:10])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Product 1

HCID 203906114-(Chloromethyl)pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene, 4-hydroxymethylpyridine-2-carbonitrile (111 mg, 0.83 mmol) synthesized in Production Example 87 was dissolved, and thionyl chloride (73 μL) was added thereto. The mixture was refluxed for 30 minutes. Thereafter, the mixture was allowed to cool down to a room temperature and stirred for one hour. After the completion of the reaction was confirmed by HPLC, the solvent was distilled off. The resulting residue was used for the next reaction without purification.

Workup

  1. dissolutionwas dissolved
  2. temperatureThe mixture was refluxed for 30 minutes
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was used for the next reaction without purification

Sources & evidence

ORD record
ord-b6fdd5c5857a43928446d3bcc2b89ac5
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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