Chlorosuccinimide → 4-(5-Chloro-2-methyl-1H-imidazol-1-yl)benzonitrile

HRID 1085148Notes

Reaction equation

HRID 1085148 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH3:14])=[CH:5][CH:4]=1)#[N:2].[Cl:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:15][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[C:10]([CH3:14])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 150053844-(2-Methyl-1H-imidazol-1-yl)benzonitrile

Product 1

HCID 200610384-(5-Chloro-2-methyl-1H-imidazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-(4-cyanophenyl)-2-methylimidazole (3 g, 16.4 mmol) and N-chlorosuccinimide (2.18 g, 16.3 mmol) in chloroform (180 ml) was heated at reflux for 4 hours, then washed with water, dried over magnesium sulphate and evaporated to a yellow solid. Trituration with ether left a pale-yellow solid (2.38 g, 67%).

Workup

  1. temperatureat reflux for 4 hours
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to a yellow solid
  5. waitTrituration with ether left a pale-yellow solid (2.38 g, 67%)

Sources & evidence

ORD record
ord-8129d1d277e145ec8eda82bcf372b7db
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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