Reaktion #430354

Reaktionsgleichung

N-Isopropyl-N-(2-methoxy-phenyl) bromoacetamide

N-phenyl phenylenediamine

potassium carbonate

→

foam

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture is filtered through celite
2. 2
   Einengenthe filtrate concentrated in vacuo
3. 3
   SonstigePurification by silica gel flash column chromatography

Vorschrift

A mixture of N-Isopropyl-N-(2-methoxy-phenyl) bromoacetamide, prepared as in Part B, (10.0 g 34.9 mmol), N-phenyl phenylenediamine (6.41 g, 34.9 mmol) and potassium carbonate (4.82 g) in DMF (100 mL) is stirred at RT for 48 h. The reaction mixture is filtered through celite and the filtrate concentrated in vacuo. Purification by silica gel flash column chromatography using 20% ethyl acetate in hexane as eluent gave N-Isopropyl-N-(2-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamideas a light brown foam (4.50 g): 1H NMR (300 MHz, CDCl3) δ7.46 (t, 1H, J=7.9), 7.030-7.05 (m, 8H), 6.98 (t, 1H, J=6.8), 6.84 (m, 2H), 6.70 (t, 1H, J=7.6), 6.37 (d, 1H, J=8.0), 5.4 (s, br, 1H), 4.95 (m, 1H, J=6.8), 3.84 (s, 3H), 3.45 (dd, 2H, J=23.2, 6.6), 1.20 (d, 3H, J=6.8), 1.01 (d, 3H, J=6.8).

Quelle