Síntese de n-arilsulfonil-ditiouretanas

Abstract

Dithiourethanes are a group of compounds derived from urethanes, by substituting the two oxygen atoms for two of sulfur. R 1 and R 2 are organic or inorganic radicals. They can be the same or different. They present low acute toxicity, low volatility and insolubility in most solvents organic, in the solid state, appear as white or light yellow solids. They find applications in livestock, agriculture, medicine, synthesis and in diverse industries and can be employed either alone or combined with other compounds. The purpose of this work was to produce derivatives of dithiourethanes introducing in its structure an arylsulfonyl group (ArSO 2) because it has important biological activities, however, N-Arylsulfonyl-dithiourethanes were synthesized in two stages: sulfonamide with carbon disulfide in basic medium, using NaOH for this purpose, in order to disodium salt is produced. In the second stage, the disodium salt obtained was subjected to methylation with dimethyl sulfate followed by hydrolysis with hydrochloric acid and washing with water until pH neutral. The compounds thus obtained were purified based on recrystallization and their purities controlled through the determination of m.p. and analysis in CCF. Its molecular structures were elucidated using FTIR. Overall, the melting temperatures of these three compounds belong to the range of 125.67 to 130.67oC and the difference between the start and end of fusion for each one is equal to 1oC. Regarding the CCF, the chromatoplate presents, in methanol, a single stain of each compound. This factor, coupled with the constant value of temperature differences gives these compounds considerable purity. However, the synthesis of N-Arylsulfonyl- ditiouretanas by the proposed method provided considerably good yields, distinctly 63.76% for N-benzenesulfonyl-S-methyl-dithiourethane, toluenesulfonyl-S-methyl-dithiourethane and 52.11% for 71.72% for N- N- (p-chloro) -benzenesulfonyl-S-methyl- ditiouretana.