Reaktion #593676

Reaktionsgleichung

(Z)-1-(3,4,5-trimethoxyphenyl)-2-(3′-nitro-4′-difluoromethoxy-phenyl)ethene

sodium thiosulphate

→

yellowish crystalline solid

Ausbeute 68.6%

(Z)-1-(3,4,5-trimethoxyphenyl)-2-(3′-amino-4′-difluoromethoxyphenyl)-ethene

Ausbeute 68.6%

Lösungsmittel

acetone water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONto dissolve all the solid
2. 2
   Temperaturthe reaction mixture was heated
3. 3
   Temperaturto reflux for 6 hours
4. 4
   Temperaturthe reaction mixture was cooled to room temperature
5. 5
   SonstigeThe organic layer was separated
6. 6
   Extraktionthe water layer was extracted with 50 ml×4 of ethyl acetate
7. 7
   Waschenwas washed with saturated brine
8. 8
   Trocknenwas dried over anhydrous magnesium sulfate
9. 9
   SonstigeThe solvent was removed by rotary evaporator partially
10. 10
    Temperaturcooled
11. 11
    Sonstigeto get crude product
12. 12
    SonstigeThe crude product was recrystallized from petroleum ether

Vorschrift

4.1 grams (10.8 mmol) of (Z)-1-(3,4,5-trimethoxyphenyl)-2-(3′-nitro-4′-difluoromethoxy-phenyl)ethene was dissolved in 10 ml of acetone/water (V/V, 2:1). The mixture was heated to 50°C., and was stirred to dissolve all the solid. 18.8 grams of sodium thiosulphate was added and the reaction mixture was heated to reflux for 6 hours. The reaction was monitored by TLC. After the reaction was completed, the reaction mixture was cooled to room temperature. The organic layer was separated, and the water layer was extracted with 50 ml×4 of ethyl acetate. The organic layer was combined and was washed with saturated brine, and then was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporator partially and then cooled to get crude product. The crude product was recrystallized from petroleum ether to give 2.6 grams of yellowish crystalline solid in a yield of 68.6%. 1H-NMR (ppm) δ: 7.08 (d, 1H, 2′-H), 6.92 (dd, 1H, 6′-H), 6.76 (d, 1H, 5′-H), 6.62 (s, 2H, 2,6-H), 6.49 (d, 1H, 1a-H), 6.43 (d, 1H, 1a′-H), 6.28 (t, 1H, J2H-F=72 Hz, —CHF2), 5.13 (broad, 2H, NH2), 3.86 (s, 3H, 4-OCH3), 3.70 (s, 6H, 3,5-OCH3).

Quelle