Chlorosuccinimide → HCID 86602469, compound

HRID 1446464Notes

Reaction equation

HRID 1446464 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-67d193025ff743529f28b48da9b2a3e5
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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