Molten-State Nitration of Substituted
Imidazoles: New Synthetic Approaches to the Novel Melt-Cast Energetic
Material, 1-Methyl-2,4,5-trinitroimidazole

Raja Duddu; Mao-Xi Zhang; Reddy Damavarapu; Nathaniel Gelber

doi:10.1055/s-0030-1260148

PAPER

Molten-State Nitration of Substituted Imidazoles: New Synthetic Approaches to the Novel Melt-Cast Energetic Material, 1-Methyl-2,4,5-trinitroimidazole

Raja Duddu*^a, Mao-Xi Zhang^a, Reddy Damavarapu*^b, Nathaniel Gelber^b
^a SAIC, U.S. Army ARDEC, Building 3028, Picatinny Arsenal, NJ 07806, USA
Fax: +1(973)3660092; e-Mail: raja.duddu@us.army.mil;
^b U.S. Army ARDEC, Building 3028, Picatinny Arsenal, NJ 07806, USA
Fax: +1(973)7245713; e-Mail: reddy.damavarapu@us.army.mil;

Abstract

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Abstract

Novel, one-step synthetic routes for the preparation of 1-methyl-2,4,5-trinitroimidazole (MTNI) are described. In addition, a new, molten-state nitration method for the synthesis of 1-methyl-2,4,5-trinitroimidazole is developed.

Key words

imidazoles - 1-methyl-2,4,5-trinitroimidazole - nitration - molten-state - solvent-free

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References

1 Mines RO. Lackey L. Introduction to Environmental Engineering Prentice Hall; Upper Saddle River NJ: 2009.

2 Okamoto Y. Chou EJ. Croce M. Freeman D. Roth M. Colitti O. Propellants, Explos., Pyrotech. 1982, 1: 18

3a Damavarapu R, Jayasuriya K, Vladamiroff T, and Iyer S. inventors; US Patent 5387297. ; Chem. Abstr. 1995, 122, 239709n

3b Duddu R, and Dave PR. inventors; US Patent 6015898.

3c Duddu R, and Dave PR. inventors; US Patent 6160113.

3d Dave PR. Duddu R. Yang K. Damavarpu R. Gelber N. Surapaneni R. Gilardi R. Tetrahedron Lett. 2004, 45: 2159

3e Dave PR, Duddu R, Damavarapu R, Gelber R, Yang K, and Surapaneni R. inventors; US Patent 6841690 B1.

3f Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 6965042 B1.

3g Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 6998485 B1.

3h Dave PR, Duddu R, Gelber N, Yang K, Surapaneni RC, and Damavarapu R. inventors; US Patent 7109359 B1.

3i Duddu R. Dave PR. Damavarapu R. Surapaneni R. Gilardi R. Synth. Commun. 2005, 35: 2709

3j Damavarapu R, Surapaneni R, Gelber N, Duddu R, Zhang M, and Dave PR. inventors; US Patent 7304164.

3k Damavarapu R. Surapaneni R. Duddu R. Farohor F. Dave PR. Parrish D. J. Heterocycl. Chem. 2007, 44: 241

3l Duddu R. Dave PR. Damavarapu R. Surapaneni R. Gilardi R. Parrish D. Synth. Commun. 2008, 38: 767

3m Duddu R. Dave PR. Damavarapu R. Surapaneni R. Parrish D. Synth. Commun. 2009, 39: 4282

3n Duddu R. Dave PR. Damavarapu R. Gelber N. Parrish D. Tetrahedron Lett. 2010, 51: 339

4a Breccia A. Cavalleri B. Adams GE. Nitroimidazoles, Chemistry, Pharmacology and Clinical Applications, In NATO Advanced Study Institute Series, Series A 42 Plenum Press; New York: 1982.

4b Nair MD. Nagarajan K. Prog. Drug Res. 1983, 27: 163

5 Novikov SS. Khmelnitskii LI. Levedev OV. Sevastyanova VV. Epishina LV. Chem. Heterocycl. Compd. (Engl. Transl.) 1970, 6: 465

6a Cho JR. Kim KJ. Cho SG. Kim JK.
J. Heterocycl. Chem. 2002, 3: 141

6b Wang W. Yang W. Ji Y. Ding F. Huozhayao Xuebao 2008, 31: 32

7 Jadhav HS. Talawar MB. Sivabalan R. Dhavale DD. Asthana SN. Krishnamurthy VN. J. Hazard. Mater. 2007, 143: 192

8a Boyer JH. Nitroazoles. The C-Nitro Derivatives of Five-Membered N- and N,O-Heterocycles, In Organic Nitro Chemistry, Series 1 VCH Publishers; Deerfield Beach / FL: 1986.

8b Larina L. Lopyrev V. Topics in Applied Chemistry. Nitroazoles: Synthesis, Structure and Applications Springer; New York: 2009.

8c Albright LF. Carr RVC. Schmitt RJ. Nitration: Recent Laboratory and Industrial Developments, ACS Symposium Series 623 American Chemical Society; Washington DC: 1996.

8d Katritzky AR. Scriven EFV. Majumder S. Akhmedova RG. Akhmedov NG. Vakulenko AV. ARKIVOC 2005, (iii): 179

8e Thottempudi V. Kim TK. Chung KH. Kim JS. Bull. Korean Chem. Soc. 2009, 30: 2152

8f Rajaraman S, and Yaqub U. inventors; US Patent 7608725 B1.

8g Agrawal JP. Hodgson RD. Organic Chemistry of Explosives John Wiley & Sons; Chichester: 2007.

9a Katritzky AR. Cundy DJ. Chen J. J. Energetic Mater. 1993, 11: 345

9b Gao H. Ye C. Gupta OD. Xiao JC. Hiskey MA. Twamley B. Shreeve JM. Chem. Eur. J. 2007, 13: 3853

10a Suwinski J. Salwinska E. Watras J. Widel M. Pol. J. Chem. 1982, 56: 1261

10b Groziak MP. Ding H. Acta Chim. Slov. 2000, 47: 1

11a Yagupol’skii LM. Maletina II. Orda VV. Zh. Org. Khim. 1974, 10: 2226

11b Hakimelahi GH. Sharghi H. Zarrinmayeh H. Khalafi-Nezhad A. Helv. Chim. Acta 1984, 67: 906

11c Effenberger F. Geke J. Synthesis 1975, 40

12 Dehmlow EV. Richter R. Zhivich AB. J. Chem. Res., Synop. 1993, 504