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

HRID 1416113Notes

Reaction equation

HRID 1416113 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:22][C:23]([N:25]([CH:32]([CH3:34])[CH3:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24]>CN(C=O)C>[CH:32]([N:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23](=[O:24])[CH2:22][NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 152160012-bromo-N-isopropyl-N-phenyl-acetamide

Product 1

HCID 10784706N-Isopropyl-N-phenyl-2-(2-phenylamino-phenylamino)-acetamideYield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (6.9 g) was added to a solution of N-phenylphenylene diamine (9.2 g) in DMF and 2-bromo-N-isopropyl-N-phenyl acetamide (12.7 g) in DMF (200 ml) and the mixture was allowed to stir overnight. The DMF was evaporated in vacuo and the residue was dissolved in ethyl acetate (400 ml) and washed exhaustively with aqueous 1N HC (4×250 ml). The organic layer was washed with water (2×200 ml), dried (Na2SO4) and evaporated to give 17.8 gm of crude alkylated product. The oil was purified by chromatography on silica gel (600 g) using first CHCl3 (8000 mL), then hexane:ethyl acetate (2:1, 8000 ml) as eluents to give the title compound (10 g), as an oil. 1H-NMR (300 MHz, CDCl3): d 7.42-6.8 (m, 14 H), 6.36 (d, 1H), 4.95 (m, 1H), 3.22 (s, 2H), 1.05 (d, 6H); MS (FAB)=360 (MH+); TLC, Rf =0.18 (CHCl3).

Workup

  1. customThe DMF was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (400 ml)
  3. washwashed exhaustively with aqueous 1N HC (4×250 ml)
  4. washThe organic layer was washed with water (2×200 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give 17.8 gm of crude alkylated product
  8. customThe oil was purified by chromatography on silica gel (600 g)

Sources & evidence

ORD record
ord-3abe54bcce0b4c87a336b8a3cec4244f
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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