반응 #430359

반응 방정식

N-Isopropyl-N-(3-methoxy-phenyl) bromoacetamide

N-phenyl phenylenediamine

potassium carbonate

→

N-Isopropyl-N-(3-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamide

용매

DMF

반응 조건

후처리

1. 1
   여과The reaction mixture is filtered through celite
2. 2
   workup.ADDITIONthe filtrate diluted with ethyl acetate (150 mL)
3. 3
   세척washed with water (2×100 mL), 2N hydrochloric acid (2×100 mL), 1N aqueous sodium hydrogen carbonate (100 mL)
4. 4
   건조dried (K2CO3 /MgSO4)
5. 5
   농축concentrated in vacuo
6. 6
   기타Purification by silica gel flash column chromatography

실험 절차

A mixture of N-Isopropyl-N-(3-methoxy-phenyl) bromoacetamide, prepared as in Part B, (12.0 g 41.9 mmol), N-phenyl phenylenediamine (7.7 g, 41.9 mmol) and potassium carbonate (5.79 g) in DMF (100 mL) is stirred at RT for 20 h. The reaction mixture is filtered through celite and the filtrate diluted with ethyl acetate (150 mL) and washed with water (2×100 mL), 2N hydrochloric acid (2×100 mL), 1N aqueous sodium hydrogen carbonate (100 mL), dried (K2CO3 /MgSO4), and concentrated in vacuo. Purification by silica gel flash column chromatography using 20% ethyl acetate in hexane as eluent gave 8.2 g of N-Isopropyl-N-(3-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamide as a light brown foam: 1H NMR (300 MHz, CDCl3) δ7.43 (t, 1H, J=8.0), 7.3-7.1 (m, 3H), 7.02 (m, 2H), 6.9-6.6 (m, 7H), 6.36 (d, 1H, J=7.8), 5.3 (s, br, 1H), 4.95 (m, 1H, J=6.8), 3.88 (s, 3H), 3.53 (s, 2H), 1.06 (m, 6H).

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