Compound 2

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InChIKey QQYQPYHQQRLTLT-UHFFFAOYSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

3,6-Bis(p-ethoxycarbonylphenyl)-1,2-diaminobenzene (1.21 g, 3.0 mmol), terephthalaldehyde (1.61 g, 12 mmol), and ZrCl₄ (70 mg, 0.30 mmol) were added to CH₃CN (100 mL). The mixture was stirred at room temperature for 24 h, 0.5 mL of triethylamine added and the solvent evaporated. The residue was extracted with CHCl₃(100 mL), the solid filtered off and the filtrate concentrated on a rotary evaporator. The pure product was obtained after two recrystallizations from CH₃CN. Yield: 0.96 g, 62%. Mp: 210–212 °C. ¹H NMR (500 MHz, DMSO-d₆): δ = 13.01 (br s, 1H, NH), 10.09 (s, 1H, CHO), 8.55 (d, 2H, Ar-H, ³J = 8.5 Hz), 8.39 (d, 2H, Ar-H, ³J = 8.5 Hz), 8.15 (d, 2H, Ar-H, ³J = 8.5 Hz), 8.13 (d, 2H, Ar-H, ³J = 8.5 Hz), 8.07 (d, 2H, Ar-H, ³J = 8.5 Hz), 7.91 (d, 2H, Ar-H, ³J = 8.0 Hz), 7.68 (d, 1H, Ar-H, ³J = 8.0 Hz), 7.46 (d, 1H, Ar-H, ³J = 8.0 Hz), 4.39 (q, 2H, COOCH₂CH₃, ³J = 7.0 Hz), 4.36 (q, 2H, COOCH₂CH₃, ³J = 7.0 Hz), 1.37 (t, 6H, COOCH₂CH₃, ³J = 7.0 Hz). ¹³C NMR (75 MHz, DMSO-d₆): δ = 193.3, 166.2, 152.2, 142.9, 142.7, 137.3, 135.5, 134.3, 130.3, 130.2, 129.7, 129.6, 129.5, 129.0, 128.5, 125.8, 124.6, 122.5, 61.4, 61.3, 14.8. HR-MS (ESI-TOF): Calculated for [M + H]⁺ [C₃₂H₂₇N₂O₅]⁺ m/z = 519.1920; found m/z = 519.1914. Elemental analysis (%): Calculated for C₃₂H₂₆N₂O₅: C, 74.12; H, 5.05; N, 5.40; found: C, 73.55; H, 5.40; N, 5.35.