Aniline → HCID 18420339, compound

Participants

Reaction Steps

C45H41F6 PS2, FW=790.90 g/mol. Aniline (2.86 g, 30.0 mmol) and 1,1,3,3-tetramethoxypropane (1.99 g, 12.1) were dissolved in acetic acid (10 mL) and heated to 80 C for 15 minutes. The solution was removed from the heat and a 60% solution of hexafluorophosphoric acid (2 mL) was slowly added. The reaction mixture was then poured into water (200 mL) and the anilinium hexafluorophosphate salt of 1,1,3,3-tetramethoxypropane, a yellow solid, was collected. Sodium acetate (0.023 g, 0.24 mmol), anilinium salt (0.044 g, 0.12 mmol), and 2-(4-Isopropylphenyl)-6-(phenyl)-4-methylthiopyrylium hexafluorophosphate (0.108 g, 0.24 mmol) are combined in a flask containing acetic anhydride (0.6 mL) and acetic acid (0.6 mL). The reaction is heated to 95 C for 8 minutes. Once the reaction is complete, the reaction mixture is poured into water and the brown precipitate is filtered off. The precipitate is dissolved in acetonitrile and crystallized out with ether. The resulting red crystals are collected in 63% yield. Melting point 165-167° C.; 1H NMR (500 MHz, CD3CN, ppm) d 7.65 (t, 2H, J=19.4 Hz), 7.34 (d, 4H, J=7.33 Hz), 7.25 (s, 10H), 7.22 (d, 4H, J=6.6 Hz), 7.09 (d, 2H, J=7.7 Hz), 6.42 (t, 1H, J=12.1 Hz), 6.23 (d, 2H, J=13.6 Hz), 2.82 (m, 2H), 1.16 (d, 12H, 7.0 Hz); UV(DCM): max 893 nm (log e 312,000±17,000 M−1 cm−1).

Provenance & Evidence