Some common heterocyclic compound, 402-46-0, name is 4-Fluorobenzenesulfonamide, molecular formula is C6H6FNO2S, 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. 402-46-0
Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline.; 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); ?3C NMR (100 MHz, CD30D) 166.6,166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9,129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 402-46-0, its application will become more common.
Reference:
Patent; MERCK & CO., INC.; WO2005/118529; (2005); A2;,
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