European Journal of Chemistry

Kinetic study of benzyl sulfamide synthesis by thermolysis of N-(benzyl)-N´-(tert-butoxycarbolyl) sulfamide



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Luciana Gavernet
Maria Luisa Villalba
Luis Bruno Blanch
Ileana Daniela Lick

Abstract

In this investigation, a kinetic study of the thermolysis of N-(benzyl)-N´-(tert-butoxycarbonyl) sulfamide to yield benzylsulfamide in an efficient manner was performed. The thermolysis reaction was monitored in helium flow by thermogravimetry at different heating rates between 0.2 and 10 oC/min. The activation energy value was obtained from the Kissinger-Akahira-Sunose isoconversional method and theoretical calculations (from Transition State Theory). The reaction model of the process was studied by means of the master-plot method. Results obtained from experiments of thermolysis performed under the melting point temperature of N-(benzyl)-N´-(tert-butoxycarbonyl) sulfamide fit with an Avrami-Erofeev model whereas data found for experiments at higher temperatures fit with first order model. Isothermal experiments were simulated at 115, 120 and 130 oC using the model-free method, employing only the activation energy value.

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Gavernet, L.; Villalba, M. L.; Blanch, L. B.; Lick, I. D. Kinetic Study of Benzyl Sulfamide Synthesis by Thermolysis of N-(benzyl)-N´-(tert-Butoxycarbolyl) Sulfamide. Eur. J. Chem. 2013, 4, 44-48.

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References

[1]. Backbro, K.; Lowgren, S.; Osterlund, K.; Atepo, J.; Unge, T.; Hulten, J.; Bonham, N. M.; Schaal, W.; Hallberg, A. J. Med. Chem. 1997, 40, 898-902.
http://dx.doi.org/10.1021/jm960588d
PMid:9083478

[2]. Hulten, J.; Bonham, N. M.; Nillroth, U.; Hansson, T.; Zuccarello, G.; Bouzide, A.; Aqvist, J.; Classon, B.; Danielson, U. H.; Karlen, A.; Kvarnstrom, I.; Samuelsson, B.; Hallberg, A. J. Med. Chem. 1997, 40, 885-897.
http://dx.doi.org/10.1021/jm960728j
PMid:9083477

[3]. Castro, J. L.; BakerGiublin, A. R.; Hobbs, S. C.; Jenkins, M. R.; Rusell, M. G.; Beer, M. S.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J. J. Med. Chem. 1994, 37, 3023-3032.
http://dx.doi.org/10.1021/jm00045a006
PMid:7932524

[4]. Acheson, R. M.; Bite, M. G.; Kemp, J. E. J. Med. Chem. 1981, 24, 1300-1304.
http://dx.doi.org/10.1021/jm00143a008

[5]. Dougherty, J. M.; Probs, D. A.; Robinson, R. E.; Moore, J. D.; Klein, T. A.; Snelgrove, K. A.; Hanson, P. R. Tetrahedron 2000, 56, 9781-9790.
http://dx.doi.org/10.1016/S0040-4020(00)00885-1

[6]. Abbate, F.; Supuran, C. T.; Scozzafava, A.; Orioli, P.; Stubbs, M. T.; Klebe, G. J. Med. Chem. 2002, 45, 3583-3587.
http://dx.doi.org/10.1021/jm011131t

[7]. Winum, J. Y.; Innocenti, A.; Nasr, J.; Montero, J. L.; Scozzafava, A.; Vullo, D.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 2353-2358.
http://dx.doi.org/10.1016/j.bmcl.2005.02.091
PMid:15837324

[8]. Casini, A.; Winum, J. L.; Montero, J. L.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2003, 13, 837-840.
http://dx.doi.org/10.1016/S0960-894X(03)00028-3

[9]. Winum, J. Y.; Cecchi, A.; Montero, J. L.; Innocenti, A.; Scozzafava, A.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2005, 15, 3302-30306.
http://dx.doi.org/10.1016/j.bmcl.2005.04.058
PMid:15908201

[10]. Maryanoff, B. E.; McComsey, D. F.; Costanzo, M. J.; Hochman, C.; Smith-Swintosky, V.; Shank, R. P. J. Med. Chem. 2005, 48, 1941-1947.
http://dx.doi.org/10.1021/jm040124c
PMid:15771438

[11]. Gavernet, L.; Barrios, I.; Sella-Cravero, M.; Bruno-Blanch, L. E. Bioorg. Med. Chem. 2007, 15, 5604-5614.
http://dx.doi.org/10.1016/j.bmc.2007.05.024
PMid:17544673

[12]. Lick, I. D.; Gavernet, L.; Bruno-Blanch, L. E.; Ponzi, E. N. Thermochim. Acta 2010, 501, 30-34.
http://dx.doi.org/10.1016/j.tca.2009.12.019

[13]. Vyazovkin, S.; Burnham, A. K.; Criado, J. M.; Perez-Maqueda, L. A.; Popescu, C.; Sbirrazzuoli, N. Thermochim. Acta 2011, 520, 1-19.
http://dx.doi.org/10.1016/j.tca.2011.03.034

[14]. Lopez-Fonseca, R.; Landa, I.; Elizundia, U.; Gutierrez-Ortiz, M. A.; Gonzalez-Velasco, J. R. Chem. Eng. J. 2007, 129, 41-49.
http://dx.doi.org/10.1016/j.cej.2006.10.029

[15]. Lopez-Fonseca, R.; Elizundia, U.; Landa, I.; Gutierrez-Ortiz, M. A.; Gonzalez-Velasco, J. R. Appl. Catal. B 2005, 61, 150-158.
http://dx.doi.org/10.1016/j.apcatb.2005.04.016

[16]. Bokova, M. N.; Decarne, C.; Abi-Aad, E.; Pryakhin, A. N.; Lunin, V. V.; Aboukais, A. Thermochim. Acta 2005, 428, 165-171.
http://dx.doi.org/10.1016/j.tca.2004.11.011

[17]. Vrandecic, N. S.; Erceg, M.; Jakic, M.; Klaric, I. Thermochim Acta 2010, 498, 71-80.
http://dx.doi.org/10.1016/j.tca.2009.10.005

[18]. Liu, L.; Jian, Y.; Li, Z.; Li, C. Thermochim Acta 2012, 54, 125-130.

[19]. Rotaru, A.; Moa, A.; Rotaru, P.; Segal, E. J. Therm. Anal. Cal. 2009, 95, 161-166.
http://dx.doi.org/10.1007/s10973-008-9070-7

[20]. Vlaev, L. T.; Markovska, I. G.; Lyubchev, L. A. Thermochim. Acta 2003, 406, 1-7.
http://dx.doi.org/10.1016/S0040-6031(03)00222-3

[21]. Vyazovkin, S.; Wight, C. A. Thermochim. Acta 1999, 340-341, 53-68.
http://dx.doi.org/10.1016/S0040-6031(99)00253-1

[22]. HyperChem(TM) Professional 7. 51., Hypercube, Inc.; 1115 NW 4th Street, Gainesville, Florida 32601, USA.

[23]. Vyazovkin, S. Int. J. Chem. Kinet. 1996, 28, 95-101.
http://dx.doi.org/10.1002/(SICI)1097-4601(1996)28:2<95::AID-KIN4>3.0.CO;2-G

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