152628-02-9, A common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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.
In a 500 mL four-necked flask equipped with a mechanical stirrer and a thermometer, 30.0 g (98.6 mmol) of 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole, 124 g of methylpyrrolidone and 11.1 g (98.9 mmol) of potassium tert-butoxide were added and stirring was started. While cooling the 4-necked flask with ice water, a solution of 33.1 g (108.5 mmol) of 4′-bromomethylbiphenyl-2-carboxylic acid methyl ester in 124 g of N-methylpyrrolidone was heated at an internal temperatureWas added dropwise at 0 to 10 C. over 25 minutes.After the dropwise addition, the mixture was stirred at an internal temperature of 0 to 10 C. for 3 hours.The reaction solution was sampled and analyzed by HPLC. As a result, 2-n-propyl-4-methyl-6- (1′-methylbenzimidazol-2-yl) benzimidazole was not detected and 82.5%4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2-propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- there were.150 g of water and 130 g of toluene were placed in a 1000 mL four-necked flask equipped with a mechanical stirrer, and while stirring,A reaction solution of a 500 mL four-necked flask was added dropwise.30 g of 35% hydrochloric acid was added to acidify the aqueous layer, and the organic layer and the aqueous layer were separated.209 g of toluene and 46 g of 25% sodium hydroxide aqueous solution were added to the aqueous layer,The aqueous layer was made alkaline and separated into an organic layer and an aqueous layer.An aqueous layer and 78 g of toluene were put into a 500 mL separating funnel and extracted,It was separated into an organic layer and an aqueous layer.The organic layers were combined and concentrated,A solution of 4 ‘- [[4-methyl-6- (1 -methyl- 1 H- benzimidazol-2-yl) -2- propyl- 1 H- benzimidazol- 1 – yl] methyl] biphenyl- 63.3 g of crude product was obtained. This crude product contained about 13.5 g of toluene, and the content of the target product was 49.8 g (yield 95.6%).
The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DNP FINE CHEMICALS UTSUNOMIYA COMPANY LIMITED; MATSUMOTO, TAKAFUMI; IKEDA, SHIN; SUZUKI, YOSHINOBU; (12 pag.)JP5711888; (2015); B2;,
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