Application of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: The syntheses of the ferrocenyl phenylguanidines were achieved in four steps (Scheme-1 suppl). In the first step; nitrophenylferrocene (a and b) were made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst [20]. In the second step; these nitro phenyl ferrocene were reduced into ferrocenylaniline (c and d) using palladium on charcoal and hydrazine as reducing agent [21]. In the third step three different chloro-substituted thioureas (e) were synthesized by the coupling of substituted aniline with thiocynates in acetone [22]. In the fourth step; the benzoylphenylthiourea (e) were mixed with the ferrocenyl aniline (c and d) in dimethyl formamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et3N). The temperature was maintained below 5C using an ice bath and one equivalent of mercuric chloride (HgCl2) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30min while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl3, 20ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH2Cl2, 20ml), washed with water (4×30ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and residue was purified by column chromatography to afford ferrocenyl phenylguanidines (f and g) [23]. Solid and liquid state characterization data is given in Supplemental part
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dichloroaniline, its application will become more common.
Reference:
Article; Gul, Rukhsana; Badshah, Amin; Khan, Azim; Junaid, Asif; Rauf, Muhammad Khawar; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 117; (2014); p. 264 – 269;,
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