Reaktion #10811

Reaktionsgleichung

4-acetyl-benzamide

2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde

lithium methoxide

→

title compound

Ausbeute 57.1%

4-{3E-[4-Methoxy-2-(2-morpholin-4-yl-ethoxy)-5-thiophen-2-yl-phenyl]-acryloyl}-benzamide

Ausbeute 57.1%

Lösungsmittel

DMF

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with water after 2 hours
2. 2
   ExtraktionThe aqueous solution was extracted with ethyl acetate
3. 3
   ExtraktionThe combined extract
4. 4
   Waschenwas washed with NaHCO3, NH4Cl, brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   workup.STIRRINGThe residue was stirred in ethanol overnight

Vorschrift

To a solution of 4-acetyl-benzamide (Ex-92A, 0.25 g, 1.53 mmol) and 2-(2-morpholin-4-yl-ethoxy)-4-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-60A, 0.53 g, 1.53 mmol) in DMF (7 mL) and methanol (3 mL) was added lithium methoxide. The solution was allowed to stir at ambient temperature. The reaction was quenched with water after 2 hours. The aqueous solution was extracted with ethyl acetate. The combined extract was washed with NaHCO3, NH4Cl, brine, dried (Na2SO4) and concentrated. The residue was stirred in ethanol overnight to afford the title compound as a yellow solid (0.43 g, 57%), mp 183–184° C. 1H-NMR (CDCl3) δ 8.09–8.04 (m, 3H), 7.93 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.57 (d, J=15.7 Hz, 1H), 7.42 (d, J=3.9 Hz, 1H), 7.32 (d, 4.4 Hz, 1H), 7.11–7.08 (m, 1H), 6.55 (s, 1H), 6.25 (bs, 1H), 5.75 (bs, 1H), 4.25 (t, J=5.9 Hz, 2H), 3.98 (s, 3H), 3.71 (t, J=4.2 Hz, 4H), 2.92 (t, J=5.7 Hz, 2H), 2.59 (t, J=4.6 Hz, 4H). MS m/z=493 ([M+H]+, 100%).

Quelle