Skip to main content

Advertisement

SpringerLink
Log in

Thermal and Crystallographic Studies of tert-Butyl 2-amino-1H-1,3-benzodiazole-1-carboxylate

  • Research Article
  • Published:
Proceedings of the National Academy of Sciences, India Section A: Physical Sciences Aims and scope Submit manuscript

Abstract

tert-Butyl 2-amino-1H-1,3-benzodiazole-1-carboxylate was synthesized by the reaction of di-tert-butyl dicarbonate with 2-aminobenzimidazole in good yield. The compound was characterized by FT-NMR, FT-IR and single crystal X-ray diffraction. The compound crystallized in orthorhombic lattice with Pbca space group and having unit cell parameters of a = 15.5303(6) Å, b = 9.3643(4) Å, c = 17.2112(7) Å, V = 2503.03(18) Å3, Dx = 1.238 mg m−3 and Z = 8. The crystal structure of compound was stabilized by N–H···N and C–H···O intermolecular interactions. The molecules are arranged into zig-zag manner in a dimeric form by N2–H1A···N1 and C12–H12C···O intermolecular hydrogen bonding which exhibited center of symmetric \( {\text{R}}^{2}_{2} (8) \) and chain \( \text{C}^{1}_{1} (8) \) patterns respectively. The thermal analysis of crystal was determined by DSC and TGA.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Tanious FA, Hamelberg D, Bailly C, Czarny A, Boykin DW, Wilson WD (2004) DNA sequence dependent monomer-dimer binding modulation of asymmetric benzimidazole derivatives. J Am Chem Soc 126:143–153

    Article  Google Scholar 

  2. Chandra T, Brown KL (2008) Vitamin B12 and α-ribonucleosides. Tetrahedron 64:9–38

    Article  Google Scholar 

  3. Kedar MS, Dighe NS, Pattan SR, Musmade DS, Thakur D, Bhosale M, Gaware VM (2010) Benzimidazole in medicinal chemistry: an overview. Der Pharma Chemica 2(2):249–256

    Google Scholar 

  4. Devereux M, McCann M, Shea DO, Kelly R, Egan D, Deegan C, Kavanagh K, McKee V, Finn G (2004) Synthesis, antimicrobial activity and chemotherapeutic potential of inorganic derivatives of 2-(4′ thiazolyl)benzimidazole{thiabendazole}: X-ray crystal structures of [Cu(TBZH)2Cl]ClH2O EtOH and TBZH2NO3(TBZH = thiabendazole). J Inorg Biochem 98:1023–1031

    Article  Google Scholar 

  5. Bagchi S (2007) Bendamustine for advanced sarcoma. Lancet Oncol 8:674

    Article  Google Scholar 

  6. Pankey GA, Sabath LD (2004) Clinical relevance of bacteriostatic versus bactericidal mechanisms of action in the treatment of Gram-positive bacterial infections. Clin Infect Dis 38:864–870

    Article  Google Scholar 

  7. Sun SX, Lee KY, Bertram CT, Goldstein JL (2007) Withdrawal of COX-2 selective inhibitors rofecoxib and valdecoxib: impact on NSAID and gastroprotective drug prescribing and utilization. Curr Med Res Opin 23:1859–1866

    Article  Google Scholar 

  8. Settimo AD, Settimo FD, Marine AM, Primofiore G, Salerno S, Viola G, Via LD, Magno SM (1998) Synthesis, DNA binding and in vitro antiproliferative activity of purinoquinazoline, pyridopyrimidopurine and pyridopyrimidobenzimidazole derivatives as potential antitumor agents. Eur J Med Chem 33:685–696

    Article  Google Scholar 

  9. Beaulieu C, Wang Z, Denis D, Grieg G, Lamontagne S, O’Neill G, Slipetz D, Wang J (2004) Benzimidazoles as new potent and selective DP antagonists for the treatment of allergic rhinitis. Bioorg Med Chem Lett 14:3195–3199

    Article  Google Scholar 

  10. Demirayak S, Mohsen UA, Karaburun AC (2002) Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. Eur J Med Chem 37:255–260

    Article  Google Scholar 

  11. Huang ST, Hsei IJ, Chen C (2006) Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorg Med Chem 14:6106–6119

    Article  Google Scholar 

  12. Ozkay Y, Tunali Y, Karaca H, Isikdag I (2010) Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety. Eur J Chem 45:3293–3298

    Article  Google Scholar 

  13. Guida X, Jianhua H, Xiaomin L (2006) Synthesis and QSAR studies of novel 1-substituted-2-aminobenzimidazoles derivatives. Eur J Chem 41:1080–1083

    Article  Google Scholar 

  14. Chaudhary M, Pareek P, Kant K, Ojha KG (2009) Conventional and microwave-induced synthesis of biologically active 1,4-dihydropyridine derivatives containing benzothiazolyl moiety. Main Group Chem 8:323–335

    Article  Google Scholar 

  15. Pattan SR, Suresh Ch, Pujar VD, Reddy VVK, Rasal VP, Kothi BC (2005) Synthesis and antidiabetic activity of 2-amino[5′(4-sulphonylbenzylidine)-2,4-thiazolidinedione]-7-chloro-6-fluorobenzothiazole. Indian J Chem 44B:2404–2408

    Google Scholar 

  16. Kálai T, Balog M, Szabó A, Gulyás G, Jeko J, Sümegi B, Hideg K (2009) New poly(ADP-ribose) polymerase-1 inhibitors with antioxidant activity based on 4-carboxamidobenzimidazole-2-ylpyrroline and-tetrahydropyridine nitroxides and their precursors. J Med Chem 52:1619–1629

    Article  Google Scholar 

  17. Rani R, Makrandi JK (2009) New poly (ADP-ribose) polymerase-1 inhibitors with antioxidant activity based on 4-carboxamidobenzimidazole-2-ylpyrroline and tetrahydropyridine nitroxides and their precursors. Indian J Chem 48B:1614–1617

    Google Scholar 

  18. Apodaca R, Dvorak CA, Xiao W, Barbier AJ, Boggs JD, Wilson SJ, Lovenberg TW, Carruthers NI (2003) A new class of diamine-based human histamine H3 receptor antagonists: 4-(aminoalkoxy)benzylamines. J Med Chem 46:3938–3944

    Article  Google Scholar 

  19. Singh MK, Gangwar M, Kumar D, Tilak R, Nath G, Agarwal A (2014) In vitro antimicrobial activity of o-phenylenediamine-tert-butyl-N-1,2,3-triazole carbamate analogs. Med Chem Res 23:4962–4976

    Article  Google Scholar 

  20. Singh MK, Tilak R, Nath G, Awasthi SK, Agarwal A (2013) Design, synthesis and antimicrobial activity of novel benzothiazole analogs. Eur J Med Chem 63:635–644

    Article  Google Scholar 

  21. Dixit SK, Mishra N, Sharma M, Singh S, Agarwal A, Awasthi SK, Bhasin VK (2012) Synthesis and in vitro antiplasmodial activities of fluoroquinolone analogs. Eur J Med Chem 51:52–59

    Article  Google Scholar 

  22. Agarwal A, Singh MK, Singh S, Bhattacharya S, Awasthi SK (2011) N-(Prop-2-yn-1-yl)-1,3-benzothiazol-2-amine. Acta Cryst E67:o2637–o2638

    Google Scholar 

  23. Singh MK, Agarwal A, Awasthi SK (2011) Benzyl N-(3-chloro-4-fluorophenyl)-carbamate. Acta Cryst E 67:o1137

    Article  Google Scholar 

  24. Singh S, Singh MK, Agarwal A, Awasthi SK (2011) 2-(4-Chlorophenyl) chromen-4-one. Acta Cryst E 67:o3163

    Article  Google Scholar 

  25. Singh MK, Agarwal A, Mahawara C, Awasthi SK (2011) tert-Butyl N-{2-[bis(prop-2-yn-1-yl)-amino]phenyl}carbamate. Acta Cryst E 67:o1382

    Article  Google Scholar 

  26. Singh S, Singh MK, Agarwal A, Hussain F, Awasthi SK (2011) (2E)-1-(4-Aminophenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one. Acta Cryst E67:o1616–o1617

    Google Scholar 

  27. Agarwal A, Singh MK, Awasthi SK (2011) 1-Prop-2-ynyl-1H-benzimidazol-2-amine. Acta Cryst E67:o3213–o3214

    Google Scholar 

  28. Mahawar C, Singh MK, Agarwal A (2013) Crystal structure of 4-[3-(4-fluoro-phenyl)-acryloyl]-phenyl-carbamic acid tert-butyl ester. Proc Natl Acad Sci Sect A Phys Sci 83:207–212

    Article  Google Scholar 

  29. Kant R, Maiti B, Awasthi SK, Agarwal A (2014) Hydrogen bonding patterns and DFT studies of (4-acetylphenyl)amino 2,2-dimethylpropanoate and (E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one. J Chem Cryst 44:421–434

    Article  Google Scholar 

  30. Schmidt GMJ (1971) Photodimerization in the solid state. Pure Appl Chem 27:647–678

    Article  Google Scholar 

  31. Thomas JMP (1974) The interaction of gases and solid surfaces. Trans R Soc Lond Ser A 277:251–286

    Article  ADS  Google Scholar 

  32. Desiraju GR (1989) Crystal engineering: the design of organic solids. J Appl Cryst 24:265

    Google Scholar 

  33. Suda Y, Arano A, Fukui Y, Koshida MW, Nishimura T, Kusumoto S, Sobel M (2006) Immobilization and clustering of structurally defined oligosaccharides for sugar chips: an improved method for surface plasmon resonance analysis of protein–carbohydrate interactions. Biconjug Chem 17:1125–1135

    Article  Google Scholar 

  34. Diffraction Oxford (2009) CrysAlis PRO. Oxford Diffraction Ltd, Yarnton

    Google Scholar 

  35. Sheldrick GM (2008) A short history of SHELX. Acta Cryst A64:112–122

    Article  Google Scholar 

  36. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, van de Streek J (2006) Mercury: visualization and analysis of crystal structures. J Appl Cryst 39:453–457

    Article  Google Scholar 

  37. Spek AL, PLATON (2003) Single-crystal structure validation with the program PLATON. J Appl Cryst 36:7–13

    Article  Google Scholar 

  38. Ghosh A, Sarkar A, Mitra P, Banerji A, Banerji J, Mandal S, Das M (2010) Crystal structure and DFT calculations of 3,4-seco-lup-20(29)-en-3-oic acid isolated from Wrightia tinctoria: stacking of supramolecular dimers in the crystal lattice. J Mol Struct 980:7–12

    Article  ADS  Google Scholar 

  39. Unver H, Yıldız M, Kiraz A, Ocak N, Erdonmez A, Dulger B, Durlu TN (2006) Spectroscopic studies, antimicrobial activities, and crystal structure of N-[2-hydroxy-1-naphthylidene] 3, 5-bis (trifluoromethyl) aniline. J Chem Cryst 36:229–237

    Article  Google Scholar 

  40. Etter MC (1990) Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23:120–126

    Article  Google Scholar 

  41. Etter MC, MacDonald JC, Bernstein J (1990) Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Cryst B46:256–262

    Article  Google Scholar 

  42. Bernstein J, Davis RE, Shimoni L, Chang N (1995) Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew Chem Int Ed 34:1555–1573

    Article  Google Scholar 

Download references

Acknowledgments

Authors are thankful to Banaras Hindu University, Varanasi, UP India for financial support and also thankful to Department of Chemistry, Banaras Hindu University Varanasi, for providing NMR, IR and single crystal X-ray diffraction facilities.

Author information

Authors and Affiliations

  1. Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi, U.P., 221005, India

    Vishal Singh, Rama Kant & Alka Agarwal

Authors
  1. Vishal Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rama Kant
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Alka Agarwal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alka Agarwal.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Singh, V., Kant, R. & Agarwal, A. Thermal and Crystallographic Studies of tert-Butyl 2-amino-1H-1,3-benzodiazole-1-carboxylate. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 86, 7–13 (2016). https://doi.org/10.1007/s40010-015-0240-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40010-015-0240-2

Keywords

Search

Navigation