Analyzing the synthesis route of 4-(2-Oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)butanoic acid

3273-68-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3273-68-5 as follows.

Preparation 4; 5,6-Dihydroimidazor4.5.1-/7c1f1lbenzazepine-2,7(1H,4H)-dione; To a solution of the compound of Preparation 5 (45.0 g, 0.2 mol) in dichloromethane (150 ml) was added thionyl chloride (30 ml, 0.4 mol) and the reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and to the residue was added dichloromethane (1000 ml) and aluminium chloride (84.0 g, 0.6 mol), added portionwise. After stirring at room temperature overnight, the reaction mixture was heated under reflux for 2 h and then concentrated in vacuo. To the residue was added ice water (2000 ml) and concentrated hydrochloric acid (50 ml), followed by additional ice water(2000 ml). The resulting precipitate was collected by filtration, washed with water (4 x 250 ml) and dissolved in sodium hydroxide solution (1 N, 600 ml). The solution was washed with dichloromethane (2 x 150 ml) and cyclohexane (150 ml) and adjusted to pH 10 by addition of dry ice. The solid material was collected by filtration, washed with water (3 x 50 ml) and dried overnight at 40C to give the title compound (30.0 g).1H-NMR (cfe-DMSO): 2.03 – 2.11 (2H), 2.90 – 3.00 (2H), 3.85 – 3.95 (2H), 7.02 – 7.10 (1 H), 7.17 – 7.24 (1 H), 7.50 – 7.58 (1 H)

According to the analysis of related databases, 4-(2-Oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)butanoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2008/44127; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem