Stearic acid was reacted with thiosemicarbazide in the presence of phosphorous oxychloride (POCl3) to produce 2-amino-5-heptadecyl-1,3,4-thiadiazole (1). Reaction of (1) with acetic anhydride, chloroacetyl chloride, phenyl isocyanate, produced acetamido, chloroacetamido, and urea derivatives of thiadiazole (2-4). Benzyl derivative (Schiff,s base) (6) and phthalimido derivative (5) of thiadiazole were obtained on treatment of 2-aminothiadiazole (1) with p-chloro benzaldehyde and tetrabromo phthalic anhydride, respectively. 6-chloro-2-heptadecylimidazo[2,1-b][1,3,4] thiadiazole (8) was obtained after cyclization of thiazolyl acetic acid (7) with phosphorous oxychloride. Most of the above synthesized compounds bearing active hydrogen atom (NH or OH) which have been ethoxylated by ethylene oxide in different molar ratios (3, 5 and 7 moles) produced nonionic surfactants having a long chain of molecular weight suitable for becoming an amphiphilic molecule with the proper hydrophilic-lypophilic balance enhancing the solubility, biodegradability and hence lowering the toxicity to humans; therefore menthioned surfactants are also friendly to the environment . All the synthesized compounds were screened as antibacterial, antifungal and antiyeast in comparison with the reference market drug (Furazol). |
