Electric Literature of 15965-31-8,Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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.
Synthesis of 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole To a stirred solution of 1-chloro-2-methoxy-4-nitrobenzene (4 g, 39.21 mmol) in DMSO (40 mL) under an argon atmosphere were added 4-chloro-1H-imidazole (7.3 g, 39.21 mmol) and potassium hydroxide (2.2 g, 39.21 mmol) at RT. The reaction mixture was stirred at 80 C. for 20 h. After consumption of the starting material (monitored by TLC), the reaction was diluted with water (600 mL), filtered, washed with water (2*50 mL) and dried in vacuo to afford 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole (3.8 g, 70%) as a brown solid which was used without further purification. 1H-NMR (CDCl3, 400 MHz): delta 7.98-7.94 (m, 2H), 7.75 (s, 1H), 7.44 (d, 1H), 7.19 (s, 1H), 4.01 (s, 3H); LC-MS: 254.1 (M+1); (column; X-Bridge C-18 (50*3.0 mm, 3.5 lam); RT 3.05 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 30% EtOAc:hexanes (Rf: 0.5).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-1H-imidazole, its application will become more common.
Reference:
Patent; FORUM Pharmaceuticals Inc.; Burnett, Duane A.; Bursavich, Matthew Gregory; McRiner, Andrew J.; (484 pag.)US2017/44182; (2017); A1;,
Imidazole – Wikipedia,
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