Water → HCID 72554651, compound

Participants

Reaction Conditions

Reaction Steps

To 107.2 g (800 mmol) of benzene-1,4-dicarboxaldehyde suspended in 450 mL methanol was added with stirring 294.0 g of 31% aqueous sulfuric acid (50 mL of concentrated sulfuric acid was added slowly to 200 mL of water while stirring). The solid dissolved and a yellow solution was obtained. The solution was heated to 80° C. with an oil bath, and 25.0 g (200 mmol) 6-methyl-[1,3,5]triazine-2,4-diamine powder was added. The solution was stirred at 80° C. for 8 h then cooled to room temperature. Next, 1.2 g of yellow byproduct (1,4-bis[4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]]-benzene) was removed by filtration, and the filtrate was treated with 2000 mL water. The resulting solid was collected by filtration and washed with saturated aqueous NaHCO3 and water until neutral. The excess benzene-1,4-dicarboxaldehyde was removed by sonicating and washing with acetone three times. Yield: 20.0 g of light yellow product. Yield=41%. 1HNMR (500 MHz, DMSO): δ9.992 (s, 1H), 7.894 (d, J=8.0 Hz, 2H), 7.847 (d, J=7.5 Hz, 2H), 7.806 (d, J=15.5 Hz, 1H), 6.928 (d, J=15.5 Hz, 1H), 6.806 (br, 4H). 13CNMR (500 MHz, DMSO): δ 193.914, 193.417, 170.671, 167.847, 141.836, 136.833, 131.461, 130.688, 128.883.

Provenance & Evidence