Chloroform → 3-(4,5-dichloro-1H-imidazol-2-yl)pyridine

HRID 1439247Notes

Reaction equation

HRID 1439247 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8]C=[CH:10][N:11]=2)[CH:2]=1.[Cl:12]N1C(=O)CCC1=O.[CH:20]([Cl:23])(Cl)Cl>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:20]([Cl:23])=[C:10]([Cl:12])[N:11]=2)[CH:2]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 123955003-(1H-Imidazol-2-yl)pyridine

Product 1

HCID 213989023-(4,5-dichloro-1H-imidazol-2-yl)pyridine

Procedure

To a suspension of 2-(3-pyridyl)-imidazole (1.5 g., 0.01 moles) in chloroform (150 ml.) is added dropwise with stirring over one hour at reflux N-chlorosuccinimide (2.6 g., 0.02 moles). The reaction mixture is heated three hours at reflux. After cooling, the solvent is removed at 20 mm. and the residue triturated with water while heating on a steam bath. The resulting solid is filtered and after recrystallization from acetonitrile 400 mg. of 2-(3-pyridyl)-4,5-dichloroimidazole is obtained, m.p. 237°-238° C.

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is heated three hours
  3. temperatureat reflux
  4. temperatureAfter cooling
  5. customthe solvent is removed at 20 mm
  6. customand the residue triturated with water
  7. temperaturewhile heating on a steam bath
  8. filtrationThe resulting solid is filtered
  9. customafter recrystallization from acetonitrile 400 mg

Sources & evidence

ORD record
ord-6b62ec7126eb43fb85506213ab94d354
Source dataset
uspto-grants-1977_11
Patent number
US04058614

Reaction notes

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