Chloride → N1-(4-Methoxybenzoyl)-N2-(4-ethoxybenzoyl)-1,2-benzenediamine

HRID 395796

Reaction equation

HRID 395796 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)[CH3:2].[Cl-].[CH3:14][O:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([NH:22][C:23]2[C:24]([NH2:29])=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([NH:22][C:23]2[C:24]([NH:29][C:8](=[O:10])[C:7]3[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:12][CH:11]=3)=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:21])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 120934-Ethoxybenzoic acidHCID 785232N-(2-Aminophenyl)-4-methoxybenzamide

Product 1

HCID 10715426N1-(4-Methoxybenzoyl)-N2-(4-ethoxybenzoyl)-1,2-benzenediamineYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-ethoxybenzoic acid (0.332 g, 2.00 mmol) and a few drops of N,N-dimethylformamide in methylene chloride (50 mL) cooled to 0° C. was added oxayl chloride (0.21 mL, 2.2 mmole). After 30 min reaction the mixture was warmed to room temperature and stirred for an additional 10 min. The mixture was concentrated in vacuo, and the residue dissolved in methylene chloride (10 mL), and the resulting solution added in two portions to a mixture of N1-(4-methoxybenzoyl)-1,2-benzenediamine (0.455 g, 2.00 mmol) and triethylamine (0.281 mL, 2.00 mmol) in methylene chloride (40 mL) cooled to 0° C. After 4 h, the mixture was allowed to warm to room temperature and stirred for an additional 12 h. The reaction was quenched with cold dilute aqueous hydrochloric acid (50 mL), diluted with hexane, and shaken in a separatory funnel. The organic layer was washed with cold dilute aqueous hydrochloric acid and saturated aqueous sodium bicarbonate solution. The solution was dried (magnesium sulfate), filtered, and concentrated in vacuo. Recrystallization of the residue from methylene chloride/hexane provided 317 mg (41%) of title compound.

Workup

  1. customAfter 30 min reaction the mixture
  2. temperaturewas warmed to room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionthe residue dissolved in methylene chloride (10 mL)
  5. temperaturecooled to 0° C
  6. waitAfter 4 h
  7. temperatureto warm to room temperature
  8. stirringstirred for an additional 12 h
  9. customThe reaction was quenched with cold dilute aqueous hydrochloric acid (50 mL)
  10. additiondiluted with hexane
  11. stirringshaken in a separatory funnel
  12. washThe organic layer was washed with cold dilute aqueous hydrochloric acid and saturated aqueous sodium bicarbonate solution
  13. dry with materialThe solution was dried (magnesium sulfate)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo
  16. customRecrystallization of the residue from methylene chloride/hexane

Sources & evidence

ORD record
ord-f2d489bd91f044d69915d6eb267aba19
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Linked notes

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