Sulfuric Acid → HCID 69241779, compound

Participants

Reaction Conditions

Reaction Steps

To 7.29 g (30 mmol) of 4-[2-(4,6-diamino-[1,3,5]triazin-2-yl)-vinyl]-benzaldehyde suspended in 150 mL of 1-pentanol at 130° C. was cautiously added 75 mL of hot aqueous sulfuric acid (25 mL of concentrated sulfuric acid was added to 50 mL of water with cautious while stirring). The solid dissolved immediately, and a yellow solution was obtained. To this solution, 4.61 g (36 mmol) of powdered barbituric acid was added while stirring vigorously at 140° C. Yellow precipitate appeared immediately. The mixture was slightly refluxed at 140° C. for 10 min then filtrated while it was hot. Solid washed with 50 mL of warm 1-pentanol, then suspended in 300 mL of water and neutralized with saturated aqueous NaHCO3. The solid was collected by filtration and washed with water. Yield: 9.72 g of yellow product. Yield=88%. 1HNMR (400 MHz, DMSO): δ11.519 (s, 1H), 11.375 (s, 1H), 8.378 (s, 1H), 8.234 (d, J=8.0 Hz, 2H), 7.915 (d, J=16.0 Hz, 1H), 7.857 (d, J=8.0 Hz, 2H), 7.101 (br, 4H), 7.047 (d, J=16.0 Hz, 1H). m.p.>350° C. EA found: C, 52.20; H, 3.86; N, 26.12. Calculated for C16H13N7O3.H2O: C, 52.03; H, 4.09; N, 26.55. MS (rel. abundance): M++1 (68), M++2 (13), 242.1 (5), 217.1 (6), 179.0 (15), 157.0 (30), 101.0 (55), 79.1 (100). MS (high resolution, ES+): MH+(352.1158).

Provenance & Evidence