With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.
The solution of commercial 2,4-dichloro-6-nitroaniline (621 mg) and 3-(4- chlorophenyl)glutaric anhydride (674 mg) in 1,4-dioxane (2 ml) was heated to reflux shortly and stirred at rt for Ih. The solvent was removed by distillation and the residue dried in vacuo. The oily residue was dissolved in acetic acid (6 ml) and heated to reflux. Iron powder (1.01 g) was added and the mixture stirred under reflux for 1 h. Then cone. HCI (6 ml) was added cautiously and the green-yellow solution was refluxed for additional 2 h. All volatiles were removed at the water aspirator and the residue precipitated from acetic acid/cone. HCI solution with water. The solid was collected by suction filtration and washed well with IM HCI and water. The crude was recrystallised from acetic acid to give 4-(5,7-dichloro-2- benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (325 mg) as colourless crystals.1H-NMR (500 MHz, DMSOd5): delta (ppm) = 2.70 (dd, J = 16.2, 8.9 Hz, IH), 2.79 (dd, J = 16.2, 5.9 Hz, IH), 3.35 (dd, J = 14.7, 8.3 Hz, IH), 3.43 (dd, J = 14.7, 7.6 Hz, IH), 3.83 (m, IH), 7.33 (q, J = 8.6 Hz, 4H), 7.59 (d, J = 1.6 Hz, IH), 7.73 (d, J = 1.6 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 33.39 (CH2), 39.39 (CH), 39.46 (CH2), 112.58 (CH), 119.26 (C), 123.64 (CH), 128.28 (2 CH), 128.63 (C), 129.14 (2 CH), 131,1 (br, C), 131,29 (C), 134.40 (C), 141.22 (C), 154.96 (C), 172.24 (CO). MS ( + ESI): m/z = 383 (M + H)., 53911-68-5
The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
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