Sodium Hydroxide → N1-(2,4-Dimethoxybenzoyl)-N2-(4-methoxybenzoyl)-1,2-benzenediamine

HRID 395805Notes

Reaction equation

HRID 395805 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][C:11]2[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1.[OH-].[Na+].[CH3:22][O:23][C:24]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:25]=1[C:26]([NH:17][C:12]1[C:11]([NH:10][C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:19][CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 86585763N1-(4-methoxybenzoyl)-1,2-benzenediamine hydrochloride

Product 1

HCID 10549309N1-(2,4-Dimethoxybenzoyl)-N2-(4-methoxybenzoyl)-1,2-benzenediamineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution N1-(4-methoxybenzoyl)-1,2-benzenediamine hydrochloride (558 mg, 2.08 mmol) in methylene chloride (100 mL) was added 0.5 N aqueous sodium hydroxide (8 mL) and the resulting mixture was cooled in an ice-water bath. 2,4-Dimethoxybenzoyl chloride (0.40 g, 2.0 mmol) was added slowly with vigorous stirring. The mixture was allowed to warm slowly to room temperature and stirred for 18 h. The organic layer was separated and washed with dilute aqueous sodium bicarbonate solution, dilute aqueous hydrochloric acid, and water. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo to provide 0.52 g (64%) of the title compound.

Workup

  1. temperaturethe resulting mixture was cooled in an ice-water bath
  2. customThe organic layer was separated
  3. washwashed with dilute aqueous sodium bicarbonate solution, dilute aqueous hydrochloric acid, and water
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bc47ecad68b4e3cb538228f6d384c3d
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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