Methanol → HCID 67385454, compound

Participants

Reaction Steps

3-(4-(2-(Diethylamino)ethylthio)-3-nitrophenyl)acrylic acid (1.74 g, 5.4 mmol) was suspended in methanol (25 mL) under stirring. To this solution, concentrated sulfuric acid (1.0 mL) was added. The resulted solution was heated to reflux for 19 hours. Cooling it to room temperature and the solvent was removed under reduced pressure. 100 ml water was added to dissolve the resulted residue. Cooling it with an ice-bath and adjusting the pH value to 9.0 using ammonia under stirring. (E)-methyl 3-(4-(2-(diethylamino)ethylthio)-3-nitrophenyl)acrylate was obtained as yellow solid. TLC: Rf=0.75 (DCM:MeOH=9:1); MP: 57.4° C.-59.1° C. HPLC: 92.0%; tR=9.74 min (LC/PDA: Diamonsil C18 5μ 150×4.6 mm, flow rate: 1.0 mL/min, grade: 10-100% B, 20 minutes: mobile phase A: water; mobile phase B: acetonitrile; UV254); IR (cm−1): 2967, 2926, 1720, 1639, 1604, 918. 1HNMR (400 MHz, CDCl3) δ: 8.36 (1H, s), 7.70 (1H, d, J=1.6 Hz), 7.69 (1H, d, J=16 Hz), 7.50 (1H, d, J=8 Hz), 7.27 (1H, s), 6.51 (1H, d, J=16 Hz), 3.83 (3H, s), 3.12 (2H, t, J=8 Hz); 2.83 (2H, t, J=8 Hz); 2.64 (4H, q, J=7.2 Hz), 1.07 (6H, t, J=7.2 Hz). MS (m/z): 339 (MH)+.

Provenance & Evidence