Chlorosuccinimide → HCID 86602469, compound

HRID 2247473Notes

Reaction equation

HRID 2247473 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=2[O:14][CH3:15])[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:16]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:16][C:5]1[N:1]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=2[O:14][CH3:15])[CH:2]=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 73014044HCID 73014044, compound

Product 1

HCID 86602469HCID 86602469, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a chloroform (3 mL) solution of the 4-(1H-imidazol-1-yl)-3-methoxybenzaldehyde (50 mg) obtained in Example 111, N-chlorosuccinimide (35 mg) was added, and the reaction solution was heated to reflux for 1.5 hours. The reaction mixture was allowed to be cooled and then purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), and 4-(2-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde (13 mg) and 4-(5-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde (14 mg) were obtained.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto be cooled
  4. custompurified by silica gel column chromatography (elution solvent: hexane-ethyl acetate system), and 4-(2-chloro-1H-imidazol-1-yl)-3-methoxybenzaldehyde (13 mg)

Sources & evidence

ORD record
ord-1e8ce563d0da43b4a28e387390e50dd5
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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