Thioureides of 2-(4-methyl-phenoxymethyl)benzoic acid have been synthesised by reaction of 2-(4-methyl-phenoxymethyl)benzoyl isothiocyanate with primary aromatic amines. The mentionated isothiocyanate was obtained in the reaction of the 2-(4-methyl-phenoxymethyl)benzoic acid chloride with ammonium thiocyanate. The acid chloride was prepared by reacting the coresponding acid, the 2-(4-methyl-phenoxymethyl)benzoic acid, with thionyl chloride and the aforementioned acid from potassium para-cresolate with phtalide. The reaction conditions were established to ensure the best yields. These new thioureides have been characterized by means of elemental analysis, IR and NMR spectral studies.
It is well known that many compounds bearing thioureide structure have been reported to have antimicrobial activity and some of these thioureide compounds are found to be associated with other therapeutical activities. The present application is a continuation of our research concerning the synthesis and characterization of 2-(4-methyl-phenoxymethyl)benzoic acid thioureides with antimicrobial activities. The new thioureides were obtained in three stages. In the first stage we prepared the 2-(4-methyl-phenoxymethyl)benzoic acid by reacting potassium para-cresolate with phtalide. The second stage consists in the synthesis of the 2-(4-methyl-phenoxymethyl)benzoic acid chloride and, in the third phase, the acid chloride aforementioned is refluxed with ammonium thiocyanate the resulting 2-(4-methyl-phenoxymethyl)benzoyl isothiocyanate being treated with primary aromatic amines to obtain the new compunds. We established the optimal reaction conditions for the new compounds synthesizing process of with high purity and yields. The new compounds, which are not mentioned in the literature concerning this domain, have been characterized by their physical properties (melting point, solubility) and the structures were confirmed by elemental analysis, 1H-NMR, 13C-NMR and IR spectral methods.
The aim of the present paper was the synthesis and chemical characterization of some original compounds with dibenzo[b,e]thiepine structure. The synthesis of the new compounds was performed in several stages. Thus, by reaction of phtalide with thiophenol potassium salt, we obtained the 2-phenylthiomethyl-benzoic acid. The acid was cyclized with polyphosphoric acid to the desired 6,11-dihydrodibenzo[b,e]thiepin-11(6H)-one, converted afterwards to the corresponding oxime and subsequently to the O-acyloximino-dibenzo[b,e]thiepins by acylation with various substituted benzoic acid chlorides. The oxidation of O-acyloximino-dibenzo[b,e]thiepins with hydrogen peroxide afforded the corresponding sulfones. The new compounds, four O-acyl-oximino-dibenzo[b,e]thiepins, and four O-acyl-oximino-dibenzo[b,e]thiepin-5,5-dioxides, have been characterized by their physical constants (melting point, solubility) and their structures and purity were confirmed by elemental analysis, and spectral analysis (IR, 1H-NMR, 13C-NMR).
Es werden die optimalen Synthesewege zur Herstellung von Tranquilizern der Diazepin‐Reihe angegeben und zwar für Librium (IV), Valium (VI) und Serax (VIII).
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