Kinetic study of the reactions of 2-amino-5-chlorobenzophenone with HCl in MeOH-H2O
The reaction of 2-amino-5-chlorobenzophenone (1) with 0·5-2 M HCI was studied in 1:1 (v/v) MeOH-H2O at 60 and 80 °C. Products that were isolated were characterized as 2-(N-methylamino-5-chlorobenzophenone (2), 2-amino-3,5-dichlorobenzophenone (3), 2-N-methylamino-3,5-dichlorobenzophenone (4), 2-(N,N...
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| Autores principales: | , |
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_08943230_v10_n2_p97_SbarbatiNudelman |
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| Sumario: | The reaction of 2-amino-5-chlorobenzophenone (1) with 0·5-2 M HCI was studied in 1:1 (v/v) MeOH-H2O at 60 and 80 °C. Products that were isolated were characterized as 2-(N-methylamino-5-chlorobenzophenone (2), 2-amino-3,5-dichlorobenzophenone (3), 2-N-methylamino-3,5-dichlorobenzophenone (4), 2-(N,N-dimethylamino-5-chlorobenzophenone (5), 2,4-dichloro-10-methyl-9,10-acridinone (6) and 2,4-dichloro-9,10-acridinone (7). The rates of reaction of 1 and the rates of formation of 2-5 were measured at several HCI concentrations. The methyl transfers, the chlorination and the cyclization reactions that give rise to 2-7 were unexpected under the present reaction conditions. A set of differential equations was proposed in order to calculate the rate constants for each step of this complex reaction. The proposed reaction scheme also takes into account the reaction 2→1 and permits the calculation of the rate constants for this reversible reaction. The experimental values of the rate constants for reaction of 1 were compared with those for 2 under the same reaction conditions, in order to evaluate the importance of the methyl group on the methyl transfer reactions; it was found that the methyl group is not required for the unexpected reaction to occur. © 1997 by John Wiley & Sons, Ltd. |
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