A kind of synthetic method of dithiocarbamate

Abstract

The invention belongs to the technical field of chemical synthesis and discloses a dithiocarbamate synthesis method. The dithiocarbamate synthesis method comprises that in an organic solvent, Ar-B(OH)2, NHR1R2 and carbon disulfide as raw materials and a copper salt and alkali as promoters undergo a reaction at a temperature of 60-120 DEG C for 10-24h with stirring, after the reaction, the reaction product is cooled to a room temperature, then is filtered and then is subjected to reduced pressure distillation for solvent removal so that a crude product is obtained, and the crude product is purified by column chromatography so that dithiocarbamate is obtained. The dithiocarbamate synthesis method realizes dithiocarbamate synthesis by one step, has simple and easy processes and a high product yield, utilizes cheap and easily available raw materials, has a low synthesis cost and has great industrial production values.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of dithiocarbamate. Background technique [0002] Dithiocarbamates are an important class of compounds with a variety of uses. Due to its important biological activity and physiological activity (such as antibacterial activity, antiviral activity, enzyme inhibitory activity, etc.), dithiocarbamate is widely used in pesticides (such as insecticides, herbicides) and medicines (such as fungicides, (Rafin, C.; Veignie, E.; Sancholle, M.; Postal, D.; Len, C.; Villa, P.; Ronco, G.J.Agric.Food Chem., 2000 , 48, 5283; Ronconi, L.; Marzano, C.; Zanello, P.; Corsini, M.; Miolo, G.; , 1648; Marinovich, M.; Viviani, B.; Capra, V.; Corsini, E.; , C.L.Chem.Res.Toxicol.2002,15,26; Rafin,C.; Veignie,E.; Sancholle,M.; Postel,D.; Chem. 2000, 48, 5283). Dithiocarbamates can also be used as vulcanization accelerators in rubber synthesis (Nieuwenhuizen, ...

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Problems solved by technology

[0004] In recent years, some new methods for the synthesis of dithiocarbamate have been reported, including: (1) the synthesis of dithiocarbamate by using electron-deficient alkenes, amines, and carbon disulfide (Ranu, B.C.; Saha, A. ; Banerjee, S. Eur. J. Org. Chem.2008, 519; Azizi, N.; Aryanasab, F.; Torkiyan, L.; Karmakar, B.; Banerji, J.Tetrahedron Lett.2011,52,6584), the shortcoming of this method is that the applicability of substrate functional group is poor, and the raw material alkene used needs to have strong electron withdrawing group; (2) dithio Reaction of carbamate with hypervalent iodine reagent (Chen, Z.-C.; Jin, Y.-Y.; Stang, P.J.J.Org.Chem.1987,52,4117), the synthesis method should be carried out step by step, and high price The synthesis of iodine reagent is more complicated, and the functional group adaptability of substrate is bad, and atom utilization rate is low; (3) utilize halide and carbon disulfide, amine reaction synthesis (Bhadra, S.; Saha, A.; Ranu, B.C.Green Chem. 2008,10,1224; Azizi, N.; Aryanasab, F.; Saidi, M.R.Org.Lett.2006,8, 5275); (4) three-component reaction synthesis of diazonium salt, carbon disulfide and amine (Chatterjee, T.; Bhadra, S.; Ranu, B.C.Green Chem., 2011, 13, 1837); (5) using hydrazone, carbon disulfide and amine to react with alkali (Sha, Q.; Wei, Y.-Y. Org.Biomol.Chem.2013,11,5615); (6) synthesized by using alcohol, carbon disulfide and amine under the action of Mitsunobu dehydrating agent (Chaturvedi,D.; Ray,S.Tetrahedron Lett.2006,47,1307)

[0005] Although the current research on the synthesis of dithiocarbamate has made great progress, some methods still have problems such as difficult access to raw materials, poor substrate applicability, harsh reaction conditions or cumbersome operating steps.

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