Category: 53439-88-6

Electric Literature of 53439-88-6, These common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, its 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 0 C. solution of 5-amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (4 g, 22.6 mmol) in 25 mL of CHCl3 and 25 mL of AcOH was slowly added dropwise bromine (3.5 g, 22.6 mmol). The mixture was stirred at RT for 30 min, then concentrated and purified by silica gel chromatography (1:1 EtOAc/hexanes) to afford 5-amino-6-bromo-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one as a yellow solid (3.2 g, 69%). MS (ES+) C9H10BrN3O requires: 256. found: 257 [M+H]+.

The synthetic route of 53439-88-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; Palmer, Wylie; Jones, Philip; Liu, Gang; Petrocchi, Alessia; Reyna, Naphtali; Subrumanian, Govindan; Theroff, Jay; Yau, Anne; (114 pag.)US2016/60260; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Formula: C9H11N3O

A mixture of 1.00 g (4.71 mmol) of ethyl (2-cyano-3-ethoxyprop-2-enoyl)carbamate (for preparation see: Senda, Shigeo, Hirota, Kosaku, Notani, Jiyoji; Chemical & Pharmaceutical Bulletin (1972), 20(7), 1380-8) and 835 mg (4.71 mmol) of 5-amino-1,3-dimethyl-1,3-dihydro-2H-benzimidazol-2-one in 5 ml of acetonitrile and 10 ml of DMF was stirred at reflux temperature overnight. After cooling to RT, the mixture was diluted with 150 ml of diethyl ether and the precipitate was filtered off. The filter residue was stirred with 10 ml of methanol, and the solid was filtered off, washed with a little methanol and ether and dried under high vacuum. This gave 703 mg (45% of theory) of the title compound. LC-MS (Method 1): Rt=0.53 min; m/z=298 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=3.30 (br. s, 3H), 3.36 (br. s, 3H), 7.17 (dd, 1H), 7.23-7.28 (m, 1H), 7.34 (d, 1H), 8.77 (s, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; Furstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Zubov, Dmitry; Schamberger, Jens; (69 pag.)US2016/244415; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 53439-88-6,Some common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C9H11N3O, 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.

General procedure: A mixture of aniline (19d-e) (13.0 mmol), ethyl chloroformate (2.5 mL, 26.0 mmol) and Et3N (3.6 mL, 26.0 mmol) in anhydrous THF (150 mL) was stirred at room temperature for 30 min. The solid was filtered off and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL) and the organic layer was washed with water (3 ¡Á 50mL). The organic phase was evaporated under reduced pressure to give 20d-e in quantitative yield (98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Article; Conconi, Maria Teresa; Marzaro, Giovanni; Urbani, Luca; Zanusso, Ilenia; Di Liddo, Rosa; Castagliuolo, Ignazio; Brun, Paola; Tonus, Francesca; Ferrarese, Alessandro; Guiotto, Adriano; Chilin, Adriana; European Journal of Medicinal Chemistry; vol. 67; (2013); p. 373 – 383;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem