With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.161798-01-2,Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate,as a common compound, the synthetic route is as follows.
A solution of compound NL (1.03mmol, 300mg, obtained from the method previously reported) [16] in 9 CH2Cl2 (20mL) and 10 Et3N (0.5mL) were added to a round-bottom flask. The mixture was stirred in an ice-water bath. A solution of 11 2,4-dinitrobenzene sulfonyl chloride (1.24mmol, 330mg) in CH2Cl2 (10mL) was added to the mixture dropwise over 0.5h. The mixture was stirred at 0¡ãC for 1h. The mixture then continued to be stirred at room temperature for 2h until thin layer chromatography indicated the reaction was complete. The organic phase was washed with 60mL of 12 water (3¡Á20mL) and then dried over MgSO4. The solvent was concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (eluted with hexanes to 13 ethyl acetate: hexane=1:4) to afford a yellow solid of 14 NL-S in 36.9percent yield (197mg, 0.38mmol). Melting point: 185.4?186.0¡ãC. 1H NMR (600MHz, DMSO?d6): delta 10.12 (s, 1H, -CHO), 9.12 (d, J=2.4Hz, 1H, ph-H), 8.63 (dd, J=8.4, 2.4Hz, 1H, ph-H), 8.46 (d, J=2.4Hz, 1H, ph-H), 8.35 (d, J=3Hz, 1H, ph-H), 8.28 (dd, J=8.1, 2.7Hz, 1H, ph-H), 7.40 (d, J=9Hz, 1H, ph-H), 4.29 (m, 2H, -CH2-), 2.68 (s, 3H, thiazole-CH3), and 1.29 (t, J=7.1Hz, 3H, -CH3). 13C NMR (150MHz, DMSO?d6): delta 188.06, 166.33, 161.59, 160.86, 152.17, 150.23, 148.54, 140.36, 134.32, 133.97, 132.68, 130.85, 129.99, 128.72, 128.17, 125.05, 121.68, 61.89, 17.60, and 14.54. High-resolution mass spectrometry (HRMS): m/z [M + Na]+ calcd. for [C20H15N3O10S2+Na]+: 544.0091, found: 544.0090. IR (KBr, cm?1): 3417.39, 3105.18, 2925.38, 1709.48, 1603.25, 1556.83, 1542.6, 1373.73, 1350.08, 1258.92, 1202.38, 1169.51, 1098.66, 887.35, 831.21, 710.78, 614.90, and 561.00., 161798-01-2
As the paragraph descriping shows that 161798-01-2 is playing an increasingly important role.
Reference£º
Article; Wang, Yi; Wang, Lijun; Jiang, Erkang; Zhu, Meiqing; Wang, Zhen; Fan, Shisuo; Gao, Qian; Liu, Shangzhong; Li, Qing X.; Hua, Rimao; Dyes and Pigments; vol. 156; (2018); p. 338 – 347;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica