Tin tetrachloride → HCID 67385624, compound

Participants

Reaction Conditions

Reaction Steps

(E)-Methyl 3-(4-(2-(diethylamino)ethylthio)-3-nitrophenyl)acrylate (736 mg, 2.2 mmol) was suspended in 15 mL solution of glacial acetic acid-Methanol. Under stirring, Tin Chloride (4.9 g, 21.7 mmol) was added and the resulted solution was heated to 0-100° C. for 0.5-5.0 hours. Cooling it then to room temperature. Removing the solvent under reduced pressure. Slowly add saturated sodium carbonate (20 mL) and dichloromethane (20 mL) to the residue with thoroughly stirring for 10-120 min. The organic layer was separated and dried with MgSO4. Removing off MgSO4 and the filtrate was concentrated into an oil. The product was purified through chromatography. 496.3 mg of (E)-methyl 3-(3-amino-4-(2-(diethylamino)ethylthio)-phenyl)acrylate was obtained. Yield: 73.9%. TLC: 0.31 (DCM:MeOH=9:1). MP: 153.2° C.-154.6° C. HPLC: 98.5%; tR=7.82 min (LC/PDA: Diamonsil C18 5μ 150×4.6 mm, flow rate 1.0 mL/min, grade: 10-100% B, 12 minutes; mobile phase A: H2O; mobile phase B: acetonitrile; UV254). 1HNMR (400 MHz, CDCl3) δ: 7.56 (1H, d, J=16 Hz), 7.39 (1H, d, J=8 Hz), 7.28 (1H, s), 6.87 (1H, dd, J=8 Hz and 16 Hz), 6.39 (1H, d, J=16 Hz), 4.51 (2H, s), 3.81 (3H, s), 3.05 (6H, m), 1.29 (6H, t, J=7.2 Hz); MS (m/z): 309 (MH)+.

Provenance & Evidence