Potassium Iodide → N-isopropyl-2-[2-(4-methoxybenzylamino)-phenylamino]-N-(4-methoxy phenyl)-acetamide

HRID 1599086Notes

Reaction equation

HRID 1599086 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(N)(=O)C.Br[CH2:31][C:32]([N:34]([CH:43]([CH3:45])[CH3:44])[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)=[O:33]>CN(C=O)C>[CH:43]([N:34]([C:35]1[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[C:32](=[O:33])[CH2:31][NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:17][CH:16]=1)([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 721779(2-Aminophenyl)(4-methoxybenzyl)amineHCID 676421992-Bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide acetamide

Product 1

HCID 18929570N-isopropyl-2-[2-(4-methoxybenzylamino)-phenylamino]-N-(4-methoxy phenyl)-acetamideYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(4-methoxybenzyl)-benzene-1,2-diamine (2.42 g, 10.6 mmol) in DMF (40 mL) was added potassium carbonate (1.47 g,10.6 mmol), potassium iodide (176 mg, 1.06 mmol), and 2-Bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide acetamide (3.03 g, 10.6 mmol). The resultant reaction mixture was stirred overnight at 60° C. The solvent was removed in vacuo and the crude material dissoved in EtOAc (150 mL), washed with water (2×50 mL) and brine (50 mL), dried with MgSO4, filtered and concentrated to a brown oil. The precipitate which formed upon the addition of ether (70 mL) was filtered to give the title compound (1.39 g, 3.21 mmol) as a yellow solid. The remaining filtrate was concentrated under reduced pressure to a brown oil which was purified by flash chromatography on silica gel (40 g) eluted with EtOAc/Hexanes (1:4, 900 mL).

Workup

  1. customThe resultant reaction mixture
  2. customThe solvent was removed in vacuo
  3. washwashed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil
  7. customThe precipitate which formed upon the addition of ether (70 mL)
  8. filtrationwas filtered

Sources & evidence

ORD record
ord-f96543f973744dbb90799fd349f0221d
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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