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 150058-27-8 as follows. category: imidazoles-derivatives
To the crude CBME (20 g, 1 eq) obtained in the above-mentioned (3) were added methanol:water [(1:1) (160 mL)] and sodium hydroxide (4.4 g, 3 eq) at 25°C – 30°C, and the reaction mixture was stirred at 75°C – 80°C for 4 hr. Using TLC (TLC: 40percent ethyl acetate/hexane, detection method: UV), complete consumption of CBME was confirmed. The reaction mixture was cooled to 25°C – 30°C, and the organic solvent was evaporated under reduced pressure at 40°C – 45°C. To the concentrated residue was added water (200 mL, 10 vol), and the aqueous layer was washed with t-butyl methyl ether (100 mL, 2×5 vol). The aqueous layer was adjusted to pH 5.5 – 6.5 by adding acetic acid (6 mL, 0.3 vol), the obtained slurry was stirred at 25°C-30°C for 1 hr, and the precipitated solid was filtered. The solid was washed with water (40 mL, 2 vol), dried with suction for 15 min, and further dried at 50°C – 55°C for 4 hr to give crude CBCA (16 g). [0327] To the obtained crude CBCA (16 g) were added ethyl acetate (160 mL, 10 vol) and dicyclohexylamine (DCHA) (8.2 g, 1.5 eq), and the mixture was stirred at 25°C – 30°C for 2 hr. The precipitated solid was filtered, washed with ethyl acetate (80 mL, 5 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a DCHA salt (16 g) of CBCA. To the salt was added isopropyl alcohol (192 mL, 12 vol) at 25°C – 30°C, and the salt was dissolved by heating to 75°C – 85°C, and the mixture was stirred for 15 min. Thereafter, the reaction mixture was cooled to 25°C – 30°C, and stirred at the same temperature for 2 hr. The precipitated solid was filtered, washed with isopropyl alcohol (32 mL, 2 vol), dried with suction for 15 min, and further blast dried at 50°C – 55°C for 4 hr to give a pure DCHA salt (13 g) of CBCA. To this salt was added 25percent aqueous sodium hydroxide solution (120 mL, 10 vol) at 25°C – 30°C, and the mixture was stirred for 15 min, adjusted to pH 5.5 – 6.5 by adding acetic acid (5.8 mL, 0.48 vol), and extracted with methylene chloride (120 mL, 2×5 vol). The extract was combined with the organic layer, and the mixture was washed with water (120 mL, 2×5 vol) and further with saturated brine (60 mL, 5 vol). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure at 40°C – 45°C to give CBCA (9 g, 47percent from BCL).
According to the analysis of related databases, 150058-27-8, the application of this compound in the production field has become more and more popular.
Reference:
Patent; API Corporation; SEKI, Masahiko; EP2891650; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem