A Simple and Novel Eco-Friendly Process for the One-Pot Synthesis of Dithiocarbamates from Amines, Carbon Disulfide, and Epoxides

Abstract

An environmentally benign, highly efficient, and simple protocol for the synthesis of various structurally divergent dithiocarbamate derivatives in one-pot reaction of amines, carbon disulfide, and epoxides, without using any solvent and catalyst at room temperature, is presented. This new procedure has the advantages of higher yield, lower cost, reduced environmental impact, and simple work-up procedure.

Key words

atom economy - dithiocarbamate - epoxide - amine - ­solvent-free

References and Notes

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13

General Procedure for the One-Pot Reaction of Amines, Carbon Disulfide, and Epoxides under Solvent-Free Conditions: The amine (4 mmol) was added slowly to the mixture of CS₂ (4 mmol) and the epoxide (3 mmol) in a test tube (Caution: reaction is very exothermic and should be controlled by slow addition of amine and maintaining the temperature around 0 °C by using an ice bath!). The reaction mixture was stirred in an ice bath for 40 min, then warmed to r.t. and stirred for 1-8 h. After the completion of the reaction, reaction mixture was diluted with EtOAc, and the organic layer was washed with H₂O. The organic layer was dried over anhyd Na₂SO₄, and the solvent was removed on the rotary evaporator to give a crude residue. The residue was purified by column chromatography if needed (EtOAc and PE) to give the pure products. All compounds were characterized on the basis of NMR spectroscopic data.