5,7-Dimethoxy-2-(3,4,5-trimethoxyphenyl)-3-((5-((2-chlorobenzyl)thio)-1,3,4-thiadiazol-2-yl)methoxy)-4H-chromen-4-one (3f)

A white solid, m. p. 112–113 °C; yield 36.6%; IR (KBr, cm⁻¹): 2997, 2942, 2838, 1636, 1603, 1578, 1572, 1505, 1490, 1470, 1454, 1415, 1350, 1245, 1211, 1164, 1127, 1108, 1018, 1003, 853, 820; ¹H NMR (500 MHz, CDCl₃) δ 7.52 (d, J = 7.4 Hz, 1H, Ar–H), 7.38–7.34 (m, 1H, Ar–H), 7.20 (m, 2H, Ar–H), 7.15 (s, 2H, Ar–H), 6.49 (d, J = 2.2 Hz, 1H, Ar–H), 6.37 (d, J = 2.1 Hz, 1H, Ar–H), 5.28 (s, 2H, CH₂), 4.45 (s, 2H, CH₂), 3.97 (s, 3H, OCH₃), 3.91 (s, 3H, OCH₃), 3.90 (s, 3H, OCH₃), 3.87 (s, 6H, 2 OCH₃); ¹³C NMR (125 MHz, CDCl₃) δ 173.3, 165.5, 164.4, 163.6, 161.2, 159.0, 154.0, 153.0, 140.2, 138.7, 134.4, 133.5, 131.6, 129.8, 129.7, 127.2, 125.1, 109.4, 106.0, 96.2, 92.6, 62.4, 61.1, 56.8, 56.4, 56.0, 34.5; HRMS (HPLC) m/z: 665.0789, found 665.0747 (([M+Na]⁺).