Some common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: 1-Methyl-1H-pyrazole-4-sulfonyl chloride
General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.11 1-Methyl-N-{1-[2-(biphenyl-2-yloxy)ethyl]piperidin-4-yl}-N-methyl-1H-pyrazole-4-sulfonamide (20) Yellow oil, 100 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.7); LC/MS purity 100%, tR = 4.65, C24H30N4O3S, MW 454.58, Monoisotopic Mass 454.20, [M+H]+ 455.5. 1H NMR (300 MHz, CDCl3) delta 1.40-1.48 (m, 2H), 1.62-1.65 (m, 2H), 2.05 (td, J = 11.90, 2.20 Hz, 2H), 2.66-2.70 (m, 2H), 2.71 (s, 3H), 2.83-2.90 (m, 2H), 3.68-3.80 (m, 1H), 3.94 (s, 3H), 4.04 (t, J = 5.63 Hz, 2H), 6.93-6.97 (m, 1H), 7.03 (td, J = 7.45, 1.06 Hz, 1H), 7.28-7.33 (m, 3H), 7.34-7.40 (m, 2H), 7.49-7.51 (m, 1H), 7.51-7.53 (m, 1H), 7.69 (d, J = 0.54 Hz, 1H), 7.73 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 28.59, 29.19, 39.57, 53.35, 55.00, 56.78, 66.94, 112.70, 121.18, 122.22, 126.83, 127.79, 128.58, 129.61, 130.86, 131.13, 131.35, 138.17, 138.48, 155.63. Anal. calcd for C24H30N4O3S·HCl: C: 58.70, H: 6.36, N: 11.41, S: 6.53; Found C: 58.96, H: 6.49, N: 11.42, S: 6.88. Mp for C24H30N4O3S·HCl: 189.5-189.9 C.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288148-34-5, its application will become more common.
Reference:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics