Document Type : Short communication


Department of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran


In this work, activated carbon sulfonic acid was prepared from the reaction of activated carbon and chlorosulfonic acid in chloroform at reflux conditions and characterized using X-ray powder diffraction (XRD) spectrum, infra-red (IR) spectrum, field emission scanning electron microscopy (FE-SEM) images and energy dispersive X-ray spectroscopy (EDS). Benzimidazole was prepared in excellent yields through the multicomponent condensation reaction of 1,2-phenylenediamine with aryl aldehydes in the presence of sulfonic acid-functionalized activated carbon (AC-SO3H), as an active catalyst, under solvent-free conditions. According to the optimized variables, the best reaction conditions for preparing benzimidazole were found to be: 0.02 gram of catalyst in solvent-free condition at 30 Min. and at 75 °C. To demonstrate the stability and durability of the catalyst, the yields of five successive runs with recovered catalyst were reported, showing no significant change in the obtained yields. Ultimately, the synthesis of benzimidazoles was achieved using an efficient, simple, environmentally benign, inexpensive and economic approach in the presence of AC-SO3H catalyst.

Graphical Abstract

Activated carbon sulfonic acid (AC-SO3H) as a green acidic catalyst for solvent-free synthesis of benzimidazole derivatives


Main Subjects

[1]. Debus H. Annal Chem Pharm., 1858, 107:199
[2]. Radziszewski B. Ber Deut Chem Ges., 1882, 15:1493
[3]. Pellei M., Gandin V., Marzano C., Marinelli M., Del Bello F. and Santini C. Appl. Organomet. Chem., 2018, 32:e4185
[4]. Naeimi H., Alishahi N. J Exp Nanosci., 2015, 10:222
[5]. Naeimi H., Alishahi N. J Ind Eng Chem., 2014, 20:2543
[6]. Sharma G.V.M., Jyothi Y. and Lakshmi P.S. Synth Commun., 2006, 36:2991
[7]. Mirjalili B.F., Bamoniri A., Mirhoseini M.A. Sci Iran., 2013, 20:587
[8]. Safari J., Khalili S.D., Banitaba S.H. Synth Commun., 2011, 41:2359
[9]. Sangshetti J.N., Kokare N.D., Kotharkar S.A., Shinde D.B. Chin Chem Lett., 2008, 19:762
[10]. Kanazawa C., Kamijo S., Yamamoto Y. J Am Chem Soc., 2006, 128:10662
[11]. a) Wang L., Sheng J., Tian H., Qian C. Synth Commun., 2004, 34:4265; b) Wang F., Tran-Dubé M., Scales S., Johnson S., McAlpine I., Ninkovic S. Tetrahedron Lett. 2013, 54:4054
[12]. Oda S., Shimizu H., Aoyama Y., Ueki T., Shimizu S., Osato H., Takeuchi Y. Org Process Res Dev., 2011, 16:96
[13]. Rezayati S., Mehmannavaz M., Salehi E., Haghi S., Hajinasiri R., Afshari Sharif Abad S. J Sci I R Iran, 2016, 27:51
[14]. Rezayati S., Abbasi Z., Rezaee Nezhad E., Hajinasiri R., Soleymani Chalanchi S. Org Chem Res., 2016, 2:162
[15]. Duan L.P., Li Q., Wu N.B., Xu D.F., Zhang H.B., Chin Chem Lett., 2014, 25:155
[16]. Shingalapur R.V., Hosamani K.M., Keri R.S. Eur J Med Chem., 2009, 44:4244
[17]. Mukherjee A., Kumar S., Seth M., Bhaduri A. P. Ind J Chem., 1989, 28:391
[18]. Bhandari K., Srinivas N., Marrapu, V.K. Bioorg Med Chem Lett., 2010, 20:291
[19]. Zang H., Su Q., Mo Y., Cheng B. W., Jun S. Ultrason Sonochem., 2010, 17:749
[20]. Tonelli M., Simone M., Tasso B., Novelli F., Biodo V. Bioorg Med Chem., 2010, 18:2937
[21]. Nasr-Esfahani M., Montazerozohori M., Abdizadeh T. Chem Pap., 2015, 69:1491
[22]. Ozkay Y., Iskar I., Incesu Z., Alkalin G. E. Eur J Med Chem., 2010, 45:3320
[23]. Hadizadeh F.H., Hosseinzadeh V., Shariaty M., Kazemi S. J Pharm Res., 2008, 7:29
[24]. Wan Y., Liu G., Zhao L., Wang H., Hung S., Chen L., Wu H. J Heterocycl Chem., 2014, 51:713
[25]. Bhragual D.D., Kumar N., Drabu S., J Chem Pharm Res. 2010, 2:345
[26]. Chawla A., Sharma A., Sharma A. K. Pharma Chem. 2012, 4:116