Synthesis and crystal structure of 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione and 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine

Abstract

The title compound 3,5-di(2-propenyl)-6-phenyl-1,3,5-triazine-2,4-dione has been synthesized by the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to orthorhombic, space group Pbca with the following crystallographic parameters: a = 16.282(4) A, b = 8.888(2) A, c = 19.281(5) A, α = 90°, β = 90°, γ = 90°, μ = 0.088 mm−1, V = 2790.1(13) A3, z = 8, Dx = 1.282 mg/m3, F(000) = 1136, T = 293(2) K, 2.11° ≤ θ ≤ 25.02°, the final R factor: R 1 = 0.0430, wR2 = 0.0981. The X-ray results demonstrate that the reaction of 6-phenyl-1,3,5-triazine-2,4-dione with allyl bromide in the presence of N,N-dimethylformamide and potassium carbonate yields the N-alkylated product. The title compound 2-dimethylamino-4-ethoxycarbonylmethoxy-6-phenyl-1,3,5-triazine has been synthesized by a new reaction, in which the solvent N,N-dimethylformamide involves. Its structure was determined by X-ray single crystal diffraction. The crystal belongs to triclinic, space group P-1 with the following crystallographic parameters: a = 7.977(2) A, b = 10.394(3) A, c = 10.837(3) A, α = 111.774(5)°, β = 104.050(5)°, γ = 99.446(5)°, μ = 0.093 mm−1, V = 776.6(4) A3, z = 2, Dx = 1.293 mg/m3, F(000) = 320, T = 293(2) K, 2.14° ≤ θ ≤ 25.03°, the final R factor: R 1 = 0.0582, wR 2 = 0.1399. The distance of N(4) $$---$$ C(2) (1.339 A) is much shorter than the length of normal C $$---$$ N (1.47 A) and very close to that of C-N (1.33 A), which is indicative of the significant double bond character.