Molbank 2007, M540

http://www.mdpi.org/molbank/

 

Microwave Induced Efficient Synthesis of 2-(1H-benzimidazol-2-ylthio)-4-methylquinoline

 

M. Raghavendra, Halehatty S. Bhojya Naik *, Tangali R. Ravikumar Naik and Bailure S. Sherigara

 

Department of PG Studies and Research in Industrial Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta- 577-451, Karnataka, India

* Author to whom correspondence should be addressed. E-mail: [email protected]

 

Received: 11 January 2006 / Accepted: 16 January 2006 / Published: 31 May 2007

 

Keywords: chloroquinoline, mercaptobenzimidazole, microwave irradiation

 

 

Quinoline derivatives posses wide class of biological activities [1-5]. Microwave heating has emerged as a powerful technique to promote a variety of chemical reaction is due to the short reaction time and the operational simplicity. So number of research paper has appeared proving the synthetic utility of MORE (Microwave-induced Organic Reaction Enhancement) chemistry in routine organic synthesis [6].

 

2-Chloro-4methylquinoline 1 (708 mg, 0.004 mol) and 2-mercaptobenzimidazole 2 (600 mg, 0.004 mol) were dissolved in minimum amount of anhydrous DMF. To this (552 mg, 0.004 mol) K2CO3 added, then the whole contents was irradiated under microwave oven for about 4 minutes at an interval of 1 min at 160 W. After the completion of reaction (monitored by TLC. ethyl acetate, pet ether 20:80), the reaction mixture was poured into ice-cold water. The obtained greenish yellow colour solid was filtered, washed with water then recrystallised from aqueous DMF, gaves 2-(1H-benzimidazol-2-ylthio)-4-methylquinoline 90 % yield.

 

Melting Point: 130-132 oC

 

MS (m/z, %): 292 ([M+H]+, 100%).

 

1H NMR (400 MHz, DMSO-d6) ¦Ä (ppm): 2.45 (3H, s, Ar-CH3), 7.22 (bs, 1H, NH), 6.90-7.92 (m, 9H, Ar−H), IR (KBr) ¦Í (cm−1): 3150 (N-H), 1250 (C-S-C), 1650 (C=N).

 

References
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