Chlorosuccinimide → 5-chloro-1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde

HRID 2194834Notes

Reaction equation

HRID 2194834 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1[CH:13]=[O:14].[Cl:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:6]1[N:2]([CH3:1])[C:3]([CH:13]=[O:14])=[N:4][C:5]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 145989821-Methyl-4-phenyl-1H-imidazole-2-carboxaldehyde

Product 1

HCID 583606175-chloro-1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde 43 (0.299 g, 1.61 mmol) in CCl4 (6 mL) was added N-chlorosuccinimide (229 mg, 1.72 mmol). The reaction mixture was heated to reflux for 4 h, cooled to room temperature, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes) gave 5-chloro-1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde 44. Mass spectrum: calculated for C1H9ClN2O 220.0; found 221.3 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (5% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1d57bbb5fd9641e585a8a14c645a9dde
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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