Azobisisobutyronitrile → 2-Chloro-4-(chloromethyl)pyridine

HRID 899959Notes

Reaction equation

HRID 899959 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Cl:28])C(=O)C1>CC#N>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:28])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 31398ChlorosuccinimideHCID 772482-Chloro-4-methylpyridine

Product 1

HCID 111265732-Chloro-4-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 g of 2-chloro-4-methylpyridine are dissolved in 30 ml of CH3CN and a mixture of AIBN (3 g) and NCS (30 g) is added. The resulting mixture is refluxed for 4 hours. After removing the solvent, the crude product is further purified by distillation (boiling point: 70° C., 20 mtorr).

Workup

  1. additionis added
  2. temperatureThe resulting mixture is refluxed for 4 hours
  3. customAfter removing the solvent
  4. distillationthe crude product is further purified by distillation (boiling point: 70° C., 20 mtorr)

Sources & evidence

ORD record
ord-a825dba2cf224593bec34cd43bbf5f21
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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