Synthesis and Identification of New Amide and ThioUrease Compounds (II)

The reaction of some new Schiff bases (2E,3Z)-3-hydrazonobutan-2-one oxime and 3-((Z)(E))-3-(hydroxyimino)butan-2-ylidene)hydrazono)butan-2-one oxime with benzoyl chloride and acetyl chloride were carried out. Subsequent reactions of these products. N-[Chloro-(2-hydroxy-phenyl)-N-(4,6diamino-[1,3,5]triazin-2-yl)-acetamide and N-[Chloro-(2-hydroxy-phenyl)-N-(4,6-diamino-[1,3,5]triazin-2yl)-benzamide with thiourea afforded thioureas compounds.The synthesized compounds were confirmed by their , UV,FTIR spectra and C.H.N. analysis .


Introduction:-
It is known that Schiff bases react smoothly with acid chlorides and anhydrides to give the corresponding addition products [1][2][3][4][5] Reaction of Schiff base with acid chloride gave imide compounds and reaction of imide compounds with thiourea afforded thioureas compounds [6] The synthesis of some new Phenobarbital compounds from the reaction of some Phenobarbital system containing Schiff bases moiety with benzoyl and 3,5-dinitro benzoyl chlorides .Subsequent reactions of these products with thiourea afforded thioureas compounds [7,9] .
However, treatment of Schiff bases with acid halides results in the formation of compounds (5-16) in which two groups (Cl ,RC=O) were introduced in the same step of the reaction. This reaction was followed by disappearance of absorption bands at (1230-1255cm-1) and ( 720-770cm-1) which were attributed to (C-N) and (C-Cl) moieties.
The reaction was involved the attack of the azomethine nitrogen by the carbonyl group of the aroyl chlorides, displacing the chloride as chloride anion and forming the iminium cation.
Moreover , the reactions of acid halides addition products (5-16) with thiourea were afforded thioureas products ( 17-26) . So , heating compounds (5-16) under reflux with thiourea in the presence of Na2CO3 for (3 hrs)led to the nucleophilic substitution of Cl by and compounds (17-26) were formed through the following mechanism (Scheme 3).
The Uv-Visible spectra showed the following maxima ( 220-240nm) and ( 300-385nm), due to the presence of aromatic rings and avariety of substituted groups.