HMBATSC synthesis

Yield:51146-75-9 96%

Reaction Conditions:

with acetic acid in methanol; for 3 h;Reflux;

Steps:

2 2.2. Synthesis of 3-methoxysalicylaldehyde thiosemicarbazone (H₂mstsc)

H₂mstsc was prepared according to a modified procedure described in the literature [20]: 3-Methoxysalicylaldehyde (0.304 g, 2 mmol) and thiosemicarbazide (0.182 g, 2 mmol) were dissolved in methanol (15 mL). Then two drops of acetic acid was added and the solution was refluxed for 3 h. The resulting white product was filtered, washed with methanol (2 * 5 mL) and dried in vacuum over CaCl₂. Yield: 0.218 g, 96%; m.p. 208 °C; FT-IR (KBr, cm^-1): ν(N-H), 3461, 3343, 3166; ν(O-H), 3032; ν(C=N), 1621; ν(C-N), 1458; ν(C-O), 1262; ν(C=S), 1120. ¹H NMR (DMSO-d₆) δ: 11.39 (s, 1H, NH), 9.18 (s, 1H, OH), 8.39 (s, 1H, H₄), 7.80 and 8.10 (2br s, 1H each, H₁), 7.52 (d, ³J_HH = 7.8 Hz, 1H, H₁₀), 6.95 (d, ³J_HH = 8.0 Hz, 1H, H₈), 6.76 (t, ³J_HH = 8.0 Hz, 1H, H₉), 3.80 (s, 3H, H₁₁). ¹³C NMR (DMSO-d₆) δ: 53.87 (C₁₁), 112.86 (C₈), 118.17 (C₁₀), 118.93 (C₉), 120.74 (C₅), 139.53 (C₄), 145.97 (C₆), 147.89 (C₇), 177.72 (C₂).

References:

Khandani, Marzieh;Sedaghat, Tahereh;Erfani, Nasrollah;Haghshenas, Mohammad Reza;Khavasi, Hamid Reza [Journal of Molecular Structure,2013,vol. 1037,p. 136 - 143]