Water → N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine

HRID 1445451Notes

Reaction equation

HRID 1445451 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[C:18]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:15].O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:13]=1[C:14]([NH:16][C:17]1[C:18]([NH:23][C:24](=[O:33])[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86628410N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetate

Product 1

HCID 86628411N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The free base form of N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine was prepared by vigorously stirring N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine trifluoroacetate (1.88 g, 3.42 mmol) with 100 ml water, 2 grams potassium carbonate and 100 ml of CH2Cl2 for several hours at room temperature. After stirring, the organic layer was set aside and combined with a 150 ml CH2Cl2 wash of the original aqueous layer. The combined CH2Cl2 extracts were washed with brine, dried over Na2SO4, concentrated in vacuo, then purified on a chromatotron system (4 mm plate) with 9:1 CH2Cl2:MeOH eluent to provide N1-[2-(2-aminoethoxy)-4-methoxybenzoyl]-N2-(4-methoxybenzoyl)-1,2-benzenediamine (1.26 g, 85%) as a brittle white foam after high vacuum drying.

Workup

  1. washwash of the original aqueous layer
  2. washThe combined CH2Cl2 extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified on a chromatotron system (4 mm plate) with 9:1 CH2Cl2

Sources & evidence

ORD record
ord-abd27750e5cc4765a1979e34fce0499e
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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