Sodium Thiosulfate → HCID 59432212, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence