Potassium Carbonate → N-Isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamide

HRID 264035Notes

Reaction equation

HRID 264035 reaction equation
[C:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([N:25]([CH:34]([CH3:36])[CH3:35])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24]>CN(C=O)C>[CH:34]([N:25]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[C:23](=[O:24])[CH2:22][NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 107795342-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

Product 1

HCID 10644060N-Isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamideYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-phenyl-benzene-1, 2-diamine(3.08 g) in DMF (35 mL) was added potassium carbonate (2.31 g) and 2-bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (4.79 g) and stirred 18 h at ambient temperature. The solvent was evaporated in vacuo and the resultant oil was dissolved in ethyl acetate (250 mL), washed with 1N HCl (4×100 mL), dried over sodium sulfate, filtered, and concentrated to a brown oil. The oil was subjected to flash chromatogaraphy on silica gel (70 g) eluted with ethyl acetate/hexanes (1:4, 1 L). Fractions containing the desired product were combined and concentrated under reduced pressure to give the title compound as a tan foam (3.95 g). 1H NMR (300 MHz, CDCl3): d 1.05 (d, J=6.9 Hz, 6H), 3.44 (s, 2H), 3.87 (s, 3H), 4.97 (m, 1H), 5.37 (br s, 1 H) 6.36 (d, J=7.4 Hz, 1H), 6.69 (t, 1H), 6.71-7.21 (m, 11H) TLC (EtOAc/Hexane (1:4)): Rf =0.18.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe resultant oil was dissolved in ethyl acetate (250 mL)
  3. washwashed with 1N HCl (4×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil
  7. washeluted with ethyl acetate/hexanes (1:4, 1 L)
  8. additionFractions containing the desired product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bbcf733055c4846abf1ba535161ffab
Source dataset
uspto-grants-1997_07
Patent number
US05646140

Reaction notes

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