Electric Literature of 152628-02-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 152628-02-9 name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
90 gm of BIM in 500 ml DMF was added at about 150C followed by addition of 41.4 gm potassium tertiary butoxide and stirred for about 15-20 minutes at 15-200C. 138.7 gm of Ethyl-4-(bromomethyl) biphenyl-2-carboxylate in 250 ml DMF was added slowly over 45 to 60 minutes maintaining temperature 15-200C. The reaction mixture was stirred for about 30 minutes. 1500 ml of Ethyl acetate and 2000 ml water were added to the reaction mixture at 20-300C and the layer was allowed to separate. Aqueous layer was extracted with 1000 ml of ethyl acetate. The combined organic layer was washed with water [3 X 1000 ml]. The organic layer was dried over anhydrous sodium sulfate and dried ethyl acetate solution was filtered. The ethyl acetate was removed by distillation under vacuum at 50-550C. 500 ml of fresh ethyl acetate was added to the residue to make a solution at 60-650C. The reaction mixture was cooled to 50-550C. 200 ml of hexane was added and stirred for 30 minutes. The reaction mixture was cooled to 100C and further stirred for about 1 hour at 5-10 C.The material was filtered and washed with a mixture of ethyl acetate and 200 ml hexane (7:3 v/vl) at 8-120C. The wet cake was dissolved in 600 ml ethyl acetate at 60-650C and cooled to ~50 0C. 240 ml of hexane was added and mixture was cooled with stirring to 100C and then stirred for about one hour. The material was filtered and washed with a mixture of 120 ml Ethyl acetate and hexane (7:3 v/v) at 8-12 C. The material was suction dried and used as such. 108.2 gm of product is obtained with 99.6 % purity (By HPLC).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, and friends who are interested can also refer to it.
Reference:
Patent; CADILA PHARMACEUTICALS LTD.; KHAMAR, Bakulesh, Mafatlal; SIDDIQUI, Ishrat, Husain; PONNAIAH, Ravi; MODI, Indravadan, Ambalal; WO2010/18441; (2010); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem