Category: 50257-40-4

Application of 50257-40-4,Some common heterocyclic compound, 50257-40-4, name is 1-((2,4,6-Triisopropylphenyl)sulfonyl)-1H-imidazole, molecular formula is C18H26N2O2S, 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.

To a stirred suspension of NaH (60percent in oil dispersion) (2.9 g, 72 mmol) in dry THF (240 mL) at 0C was added in portions 7 (3.8 g, 24 mmol), followed by 2,4,6-triisopropyl-benzenesulfonylimidazole (20 g, 60 mmol), and the whole mixture was then stirred for 3 h. Cold H2O (100 mL) was added, and the resulting mixture was extracted with EtOAc (3 × 40 mL). The combined extracts were washed with brine (50 mL) and then dried (anhydrous Na2SO4). Evaporation of the solvent gave the crude product, which contains 12 and its regioisomer 13 with a ratio of 3:1. The mixture was purified by flash chromatography on silica gel (hexane/EtOAc, 50:1) to afford 12 and 13. For 12 (4.1g, 41percent yield; colorless oil): [alpha]D20 +2.0 (c = 1.00, CH2Cl2); 94.6percent ee; 1H NMR (300 MHz, CDCl3): delta 1.04 (t, J = 7.5 Hz, 3 H), 1.22-1.29 (m, 18 H), 2.01-2.08 (m, 2 H), 2.60-2.70 (m, 2 H), 2.81 (dd, J = 2.55, 4.81 Hz, 1 H), 2.90-2.93 (m, 2 H), 3.20-3.28 (m, 1 H), 4.12-4.16 (m, 2 H), 4.50-4.54 (m, 1 H), 7.18 (s, 2 H); 13C NMR (75 MHz, CDCl3): delta 12.3, 14.0, 23.0, 23.6, 24.7, 24.8, 29.8, 34.3, 45.5, 52.4, 72.8, 79.4, 85.2, 123.8, 130.7, 150.6, 153.7; HRMS (ESI): m/z [M+Na]+ calcd for C23H34O4SNa: 429.2070; found: 429.2073. For 13 (1.3g, 14percent yield; colorless oil): 1H NMR (400 MHz, CDCl3): delta 1.08 (t, J =7.5 Hz, 3H), 1.25-1.28 (m, 18H), 2.07-2.26 (m, 3H), 2.52-2.61 (m, 1H), 2.85-2.99 (m, 1H), 3.18-3.28 (m, 2H), 4.03-4.22 (m, 3H), 4.39 (dd, J = 3.81, 11.42 Hz, 1H), 7.20 (s, 2H); 13C NMR (100 MHz, CDCl3): delta 12.4, 14.0, 19.1, 23.7, 24.8, 24.8, 29.8, 34.4, 53.5, 54.7, 67.1, 73.1, 84.9, 124.0, 129.1, 151.0, 154.1; HRMS (ESI): m/z [M+Na]+ calcd for C23H34O4SNa: 429.2070; found: 429.2073. The enantiomeric excess of 12 was determined by chiral HPLC analysis (column, Chiralpak AD-H, 4.6 mm × 250mm, n-hexane / i-PrOH = 97:3; flow rate: 0.5 mL/min, lambda = 230nm). The retention times corresponding to 12 and its enantiomer are 12.8 min and 10.2 min, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-((2,4,6-Triisopropylphenyl)sulfonyl)-1H-imidazole, its application will become more common.

Reference:
Article; Xu, Kai; Zhao, Shuai; Xu, Jia-Kuan; Shan, Ming-Wei; Yu, Jia-Li; Wang, Yu-Bo; Zhang, Cheng-Fang; Chen, Xin; Synthetic Communications; vol. 47; 20; (2017); p. 1848 – 1853;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

50257-40-4, name is 1-((2,4,6-Triisopropylphenyl)sulfonyl)-1H-imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 50257-40-4

To a stirred suspension of NaH (60percent in oil dispersion) (2.9 g, 72 mmol) in dry THF (200 mL) at 0C was added in portions 16 (2.5 g, 15.8 mmol), followed by 2,4,6-triisopropyl-benzenesulfonylimidazole (13 g, 39.6 mmol), and the whole mixture was then stirred for 3 h. Cold H2O (80 mL) was added, and the resulting mixture was extracted with EtOAc (3 × 50 mL). The combined extracts were washed with brine (50 mL) and then dried (anhydrous Na2SO4). Evaporation of the solvent gave the crude product, which was purified by flash chromatography on silica gel (hexane/EtOAc, 50:1) to afford 17 (2.5 g, 42percent yield) as colorless oil. [alpha]D20 -2.0 (c = 1.00, CH2Cl2); 96percent ee; 1H NMR (300 MHz, CDCl3): delta 1.04 (t, J = 7.5 Hz, 3 H), 1.22-1.28 (m, 18 H), 2.02-2.07 (m, 2 H), 2.62-2.68 (m, 2 H), 2.81 (dd, J = 2.5, 4.8 Hz, 1 H), 2.90-2.93 (m, 2 H), 3.22-3.25 (m, 1 H), 4.12-4.16 (m, 2 H), 4.50-4.55 (m, 1 H), 7.18 (s, 2 H); 13C NMR (75 MHz, CDCl3): delta 12.4, 13.9, 22.9, 23.6, 24.7, 24.8, 29.8, 34.3, 45.5, 52.5, 72.9, 79.4, 85.2, 123.8, 130.7, 150.6, 153.7; HRMS (ESI): m/z [M+Na]+ calcd for C23H34O4SNa: 429.2070; found: 429.2073.

The synthetic route of 50257-40-4 has been constantly updated, and we look forward to future research findings.