Reaktion #351217

Reaktionsgleichung

N-phenyl-benzene-1, 2-diamine

potassium carbonate

2-bromo-N-isopropyl-N-(4-methoxy-phenyl)-acetamide

→

title compound

Ausbeute 60.7%

N-Isopropyl-N-(4-methoxy-phenyl)-2-(2-phenylamino-phenylamino)-acetamide

Ausbeute 60.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated in vacuo
2. 2
   workup.DISSOLUTIONthe resultant oil was dissolved in ethyl acetate (250 mL)
3. 3
   Waschenwashed with 1N HCl (4×100 mL)
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to a brown oil
7. 7
   Wascheneluted with ethyl acetate/hexanes (1:4, 1 L)
8. 8
   workup.ADDITIONFractions containing the desired product
9. 9
   Einengenconcentrated under reduced pressure

Vorschrift

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.

Quelle