N-(2-Aminophenyl)-4-methoxybenzamide → N1-(4-methoxybenzoyl)-N2-(1,5-dioxo-5-morpholinopentyl)-1,2-benzenediamine

HRID 395809Notes

Reaction equation

HRID 395809 reaction equation
[O:1]=[C:2]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=O.[CH3:15][O:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([NH:23][C:24]2[C:25]([NH2:30])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:22])=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]([NH:23][C:24]2[C:25]([NH:30][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:22])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 157799485-Morpholin-4-YL-5-oxopentanoic acid

Product 1

HCID 21352763N1-(4-methoxybenzoyl)-N2-(1,5-dioxo-5-morpholinopentyl)-1,2-benzenediamineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure described in Example 161, 5-oxo-5-morpholinopentanoic acid (166 mg, 0.826 mmol) was reacted with N1-(4-methoxybenzoyl)-1,2-benzenediamine. The reaction mixture was diluted with additional methylene chloride and washed with 1 N aqueous sodium hydroxide. The organic phase was washed with 1 N aqueous hydrochloric acid, dried (sodium sulfate), filtered, and concentrated in vacuo to provide 300 mg (85%) of the title compound as an amorphous white solid.

Workup

  1. washwashed with 1 N aqueous sodium hydroxide
  2. washThe organic phase was washed with 1 N aqueous hydrochloric acid
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e3321f7c5c2454f850a9b9876657922
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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