Reference 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.
Intermediate 27: Methyl {2-[(5-chloro-1 H-imidazol-1-yl)methyl1phenyl)acetateMethyl [2-(bromomethyl)phenyl]acetate (Intermediate 1 , 3 g, 12.34 mmol) and 4-chloro- 1 H-imidazole (Intermediate 26, 3.80 g, 37.0 mmol) were dissolved in dry DMF (100 ml) and stirred at room temperature for 16 hours. After dilution with water the mixture was extracted with DCM, the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (5Og) eluting with a gradient of MeOH in DCM from 0 to 5% to afford the title compound (1.6 g, 6.04 mmol) contaminated with -10% of the regioisomer methyl {2-[(4-chloro-1 H-imidazol- 1-yl)methyl]phenyl}acetate, which was used in the next step without further purification; UPLC/MS Rt=0.50 min; m/z (ES): 265 and 267 [M+H]+ ; 1H NMR (CDCI3) only signals relating to the title compound: delta 3.71 (s, 2H), 3.72 (s, 3H), 5.21 (s, 2H), 6.92 (d, 1 H), 7.05 (d, 1 H), 7.28-7.42 (m, 4H).
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; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem