CN115010634A - A kind of dithiooxamide compound and preparation method thereof - Google Patents

Abstract

The invention provides a dithiooxamide compound and a preparation method thereof, belonging to the technical field of organic compound preparation. In the present invention, elemental sulfur, tetrachloroethane and amine monomers are mixed, heated and stirred in a solvent or under solvent-free conditions, and purified after the reaction to obtain N,N-disubstituted disulfide Oxamide compound. The invention realizes the high-efficiency and low-cost preparation of rarely reported N,N-dialiphatic substituted dithiooxamide compounds and N,N-diaryl substituted dithiooxamide compounds, and the preparation method of the invention It has the characteristics of mild reaction conditions, simple operation and diverse product structures.

Description

A kind of dithiooxamide compound and preparation method thereof

technical field

The invention relates to the technical field of organic compound preparation, in particular to a dithiooxamide compound and a preparation method thereof.

Background technique

At present, compounds containing both nitrogen and sulfur atoms, such as thiourea compounds, thioamide compounds, thiocarbamate compounds, and benzothiadiazole compounds, are widely used in the field of biomedicine, organic synthesis chemistry, coordination chemistry, Solar cells, pesticides and other fields have a wide range of applications, and the research on their synthesis and application is of great significance. Dithiooxamide compounds with similar structures have also been found to have important applications in organic synthesis chemistry, coordination chemistry and other fields, but compared with the above-mentioned compounds, there are relatively few synthetic methods for dithiooxamide compounds. , so the research on the application of dithiooxamide compounds in the aforementioned fields is also limited.

The reported preparation methods of dithiooxamide compounds can be classified into two categories: 1. Use Lawson's reagent with unpleasant taste or phosphorus pentasulfide to process oxamide compounds, and obtain the corresponding dithiooxamide compounds; 2. Use an unsubstituted dithiooxamide with an amine group to react with an amine compound to obtain a corresponding dithiooxamide compound. Lawson's reagent or phosphorus pentasulfide is unpleasant, expensive, and may replace only one oxygen atom in the oxamide compound and generate a monothiooxamide compound, while the unsubstituted amine group dithiooxamide is also more expensive, and the reaction Ammonia gas is released, which makes the production cost of the dithioxamide compound higher. Therefore, it is of great significance to develop a low-cost preparation method using inexpensive and readily available monomers to prepare dithiooxamides. Multicomponent reactions (MCRs), which have the characteristics of mild reaction conditions, simple operation, and diverse product structures, have been proven to allow cheap and readily available or abundant compounds, such as water and carbon dioxide, to effectively participate in the reaction and participate in the reaction. Construct functional molecules with complex structures. The development of the petroleum industry has increased the production and storage of elemental sulfur. However, the easy oxidation of elemental sulfur into sulfur oxides makes the storage of sulfur cause certain safety and potential environmental problems. Some multi-component reactions, such as the Willgerodt-Kindler reaction involving amine compounds, aldehyde compounds and elemental sulfur, can efficiently convert low-cost elemental sulfur into thioamide compounds, which reduces the synthesis cost of compounds containing nitrogen and sulfur elements. , and more green. Multi-component reactions, which have been shown to efficiently convert low-cost elemental sulfur into various sulfur-containing compounds such as thioamide compounds, are also expected to be used for the synthesis of dithioxamide compounds.

SUMMARY OF THE INVENTION

The purpose of the present invention is to provide a dithiooxamide compound and a preparation method of the dithiooxamide compound with low cost, mild conditions and high reaction efficiency.

In order to achieve the above-mentioned purpose of the invention, the present invention provides the following technical solutions:

The present invention provides a dithiooxamide compound, the dithiooxamide compound comprises one of the following general structural formulas:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group;

^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group;

R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent;

R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents.

Further, the dithiooxamide compound specifically includes one of the following structural formulas:

The invention provides a preparation method of a dithiooxamide compound, comprising the following steps:

The product obtained by the reaction of sulfur, tetrachloroethane and amine compounds is the dithiooxamide compound.

Further, the molar ratio of the sulfur, tetrachloromethane and the amine compound is 0.25-10.0:0.17-4.0:1.0-10.0.

Further, the amine compound comprises one of the following general structural formulas:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group;

^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group;

R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent;

R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents.

Further, the amine compound specifically comprises one of the following structural formulas:

Here, n and k are independently an integer of 1-30.

Further, the reaction is carried out in a solvent, and the molar volume ratio of the amine compound to the solvent is 0.01-5mol:1L;

The solvent contains one or more of N,N-dimethylformamide, N,N-dimethylacetamide and dimethylsulfoxide.

Further, the reaction is carried out under a protective atmosphere, and the protective atmosphere contains nitrogen and/or argon.

Further, the temperature of the reaction is 20～120°C, and the reaction time is 2～48h.

Further, the reaction is carried out under the action of a catalyst, and the catalyst is a basic compound, and the basic compound comprises N,N-diisopropylethylamine, triethylamine, potassium fluoride and potassium carbonate. One or more; the dosage of the catalyst is 10-40:1-10.

Beneficial effects of the present invention:

(1) The present invention can provide aromatic-substituted dithiooxamide compounds, but is not limited to aliphatic-substituted dithiooxamide compounds prepared by other methods.

(2) In the preparation method of the present invention, the reaction raw materials are cheap and can be purchased through commercial channels without additional synthesis steps, and the organic reaction conditions are mild, the process is simple, and the reaction efficiency is high. At the same time, the present invention can realize less one-step conversion from elemental sulfur to dithiooxamide compound.

(3) The preparation method of the present invention has good universality of reactants, is compatible with aliphatic primary amines, aliphatic secondary amines and aromatic primary amines, and can synthesize dithioxamide compounds with a wide range of structures.

(4) The preparation method of the present invention can prepare a gram-scale dithiooxamide compound at a time.

(5) The dithiooxamide compound prepared by the present invention is found to have the ability to coordinate with metal ions, indicating that the dithiooxamide compound can be applied in the field of coordination chemistry.

Description of drawings

1 is a single crystal X-ray diffraction analysis diagram of the single crystal of the dithiooxamide compound prepared in Example 2 of the present invention grown in a dichloromethane-n-hexane solvent system;

Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of the dithiooxamide compound prepared in the embodiment of the present invention 1 in deuterated dimethyl sulfoxide;

Fig. 3 is the carbon nuclear magnetic resonance spectrum of the dithiooxamide compound prepared in Example 1 of the present invention in deuterated dimethyl sulfoxide.

Detailed ways

The present invention provides a dithiooxamide compound, the dithiooxamide compound comprises one of the following general structural formulas:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group;

^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group;

R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent;

R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents.

In the present invention, R ¹ and R ² are independently preferably cyclohexyl, cyclopentyl, benzyl or phenethyl.

In the present invention, R ³ and R ⁴ are independently preferably a hydrogen atom, a methyl group or a bromine.

In the present invention, R ⁵ and R ⁶ are independently preferably cyclic alkanes having 4 to 8 carbon atoms.

In the present invention, R ⁷ and R ⁸ are independently preferably chain alkanes having 4 to 8 carbon atoms.

In the present invention, the dithiooxamide compound is preferably one of the following structural formulas:

The invention provides a preparation method of a dithiooxamide compound, comprising the following steps:

The product obtained by the reaction of sulfur, tetrachloroethane and amine compounds is the dithiooxamide compound.

In the present invention, the reaction equation of the dithiooxamide compound is the following formula (I):

Here, R ⁹ and R ¹⁰ are independently any one of R ¹ to R ⁸ .

In the present invention, the molar ratio of the sulfur, tetrachloromethane and amine compounds is 0.25-10.0: 0.17-4.0: 1.0-10.0, preferably 0.5-8.0: 0.3-3.0: 2.0-8.0, more preferably 1.0 ~6.0: 1.0 ~ 2.0: 8.0.

In the present invention, the amine compound comprises one of the following general structural formulas:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group;

^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group;

R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent;

R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents.

In the present invention, the R ¹ is preferably cyclohexyl, cyclopentyl, benzyl or phenethyl.

In the present invention, R ³ is preferably a hydrogen atom, methyl or bromine.

In the present invention, R ⁵ is preferably a cyclic alkane having 4 to 8 carbon atoms.

In the present invention, R ⁷ and R ⁸ are independently preferably chain alkanes having 4 to 8 carbon atoms.

In the present invention, the amine compound is further preferably one of the following structural formulas:

Here, n and k are independently an integer of 1-30.

In the present invention, n and k are independently preferably an integer of 5-20, more preferably an integer of 10-15.

In the present invention, the reaction is carried out in a solvent, and the molar volume ratio of the amine compound to the solvent is 0.01-5mol:1L, preferably 0.5-4mol:1L, more preferably 1-3mol:1L.

In the present invention, the solvent comprises one or more of N,N-dimethylformamide, N,N-dimethylacetamide and dimethyl sulfoxide, preferably dimethyl sulfoxide.

In the present invention, the reaction is carried out under a protective atmosphere containing nitrogen and/or argon, preferably nitrogen.

In the present invention, the reaction temperature is 20-120 °C, and the reaction time is 2-48 h; preferably, the reaction temperature is 50-100 °C, and the reaction time is 5-40 h; more preferably, the reaction time is 5-40 h. The temperature is 60～80℃, and the reaction time is 10～30h.

In the present invention, the reaction is accelerated by stirring, and the rotational speed of the stirring is 300-800 rpm, preferably 500 rpm.

In the present invention, the reaction is carried out under the action of a catalyst, and the catalyst is a basic compound, and the basic compound includes N,N-diisopropylethylamine, triethylamine, potassium fluoride and potassium carbonate One or more of them, preferably N,N-diisopropylethylamine.

In the present invention, the molar ratio of the catalyst and the amine compound is 10-40:1-10, preferably 40:10.

In the present invention, the reaction product needs to be purified after the reaction, and the purification treatment is as follows: diluting the reaction solution with ethyl acetate, filtering to remove the solid matter, and sequentially performing extraction treatment, elution treatment, and drying on the remaining liquid. The purified product was obtained.

In the present invention, the water phase of the extraction treatment is saturated aqueous ammonium chloride solution, and the oil phase is ethyl acetate; the solvent used in the elution treatment is petroleum ether and ethyl acetate with a volume ratio of 3-5:1 Esters, preferably 4:1.

In the present invention, the drying temperature is 50-70 °C, and the drying time is 10-30 min; preferably, the drying temperature is 60 °C, and the drying time is 20 min.

In the present invention, the chemicals used can be purchased from chemical reagent companies, wherein cyclohexylamine, tetrachloroethane, N,N-dimethylacetamide, N,N-diisopropylethylamine and 2-Phenylethylamine was purchased from Anaiji Company, p-methoxybenzylamine was purchased from TCI Company, piperidine was purchased from Kaixin Chemical, sulfur (sublimated sulfur) was purchased from Alfa Esa Company, and dodecylamine was purchased from Aladdin Co.

The technical solutions provided by the present invention will be described in detail below with reference to the embodiments, but they should not be construed as limiting the protection scope of the present invention.

Example 1

Cyclohexyl-substituted dithiooxamides are prepared by a multi-component reaction using elemental sulfur, tetrachloroethane and amine compounds to prepare dithiooxamide compounds. The reaction equation is as formula (II):

The synthetic method steps are as follows:

In a reactor filled with nitrogen, 8 mL of N,N-dimethylacetamide was added to 8 mmol of cyclohexylamine, 2 mmol of tetrachloroethane and 10 mmol of sulfur to dissolve it, and heated to 100 degrees Celsius and stirred at 500 rpm for 8 Hour.

After the reaction, the heating was stopped and 100 mL of ethyl acetate was added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 as the eluent and dried at 60 °C for 20 min. The yield of 3000 gave the product as an orange-red solid, the cyclohexyl-substituted dithiooxamide compound.

The dithiooxamide compound obtained in this example is shown in Compound 1.

The characterization data of the dithiooxamide compounds prepared in this example are as follows:

Dithioxamide compound, orange-red solid, yield 59%. The nuclear magnetic data are as follows: ¹ H NMR (400MHz, CDCl ₃ -d), δ (TMS, ppm): 10.35 (d, 1H, -NH-), 4.25 (m, 1H), 2.05 (m, 2H), 1.79 ( m, 2H), 1.66 (m, 1H), 1.44 (m, 4H), 1.33 (m, 1H). ¹³ C NMR (100 MHz, CDCl ₃ -d), δ (TMS, ppm): 183.09 (C=S ), 55.82, 30.64, 25.45, 24.35.

Example 2

Utilize the multi-component reaction of elemental sulfur, tetrachloroethane and amine compound to prepare dithiooxamide compound to prepare p-methoxybenzyl substituted dithiooxamide, the reaction equation is as formula (III):

The synthetic method steps are as follows:

8 mmol of p-methoxybenzylamine, 2 mmol of tetrachloroethane and 10 mmol of sulfur were added to the reactor and nitrogen gas was injected into the reactor, and the reactor was heated to 100 degrees Celsius and stirred at 500 rpm for 8 hours.

After the reaction was completed, the heating was stopped and 60 mL of ethyl acetate and 50 mL of purified water were added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography using a mixed solvent with a volume ratio of petroleum ether and ethyl acetate of 4:1 as the eluent, and dried at 60 °C for 20 min. A yield of 100% yields a yellow solid product, a p-methoxybenzyl-substituted dithiooxamide compound.

The dithiooxamide compound obtained in this example is shown in Compound 2.

As a means of proving the structure of the dithiooxamide compound obtained in Example 2, a strip-shaped single crystal of the compound was grown in a mixed solvent of dichloromethane and n-hexane with a volume ratio of 1:1, and the single crystal was analyzed. The single-crystal X-ray diffraction test was carried out, and the test results proved the structure of the dithiooxamide compound. The compound structure shown by the single-crystal X-ray diffraction analysis is shown in FIG. 1 .

Example 3

Utilize elemental sulfur, tetrachloroethane and amine compound to prepare the multi-component reaction of dithiooxamide compound to prepare p-methylphenyl substituted dithiooxamide under the condition of adding alkali reagent, the reaction equation is as formula (IV ) as shown:

The synthetic method steps are as follows:

In a reactor filled with argon, 8 mL of N,N-dimethylacetamide and 5573.7 μL of N,N-diisopropylethylamine (32.0 mmol) were added to 8 mmol of p-methylaniline, 6 mmol of tetrakis Dissolve ethyl chloride with 10 mmol of sublimed sulfur and heat to 100 degrees Celsius with stirring at 400 rpm for 8 hours.

After the reaction, the heating was stopped and 100 mL of ethyl acetate was added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography and a mixed solvent with a volume ratio of petroleum ether and ethyl acetate of 4:1 was used as the eluent, and dried at 50 °C for 10 min. The yield of 3000 gave the product as an orange-red solid, the p-methylphenyl substituted dithiooxamide compound.

The dithiooxamide compound obtained in this example is shown in Compound 3.

Example 4

The multi-component reaction of preparing dithiooxamide compound using elemental sulfur, tetrachloroethane and amine compound prepares piperidinyl-substituted fully substituted dithiooxamide, and the reaction equation is shown in formula (V):

The synthetic method steps are as follows:

In a reactor filled with argon, 8 mL of N,N-dimethylacetamide was added to 8 mmol of piperidine, 2 mmol of tetrachloroethane and 10 mmol of sulfur to dissolve, and heated to 100 degrees Celsius at 800 rpm under stirring for 8 hours.

After the reaction, the heating was stopped and 100 mL of ethyl acetate was added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 as the eluent and dried at 60 °C for 10 min. The yield of yellow solid product piperidinyl substituted fully substituted dithiooxamide compound.

The dithiooxamide compound obtained in this example is shown in Compound 4.

Example 5

The multi-component reaction of preparing dithiooxamide compound using elemental sulfur, tetrachloroethane and amine compound prepares (2-phenethyl) substituted dithiooxamide, and the reaction equation is shown in formula (VI):

The synthetic method steps are as follows:

In a reactor filled with argon, 8 mL of N,N-dimethylacetamide was added with 8 mmol of 2-phenylethylamine, 2 mmol of tetrachloroethane and 10 mmol of sulfur to dissolve, and heated to Stir at 800 rpm at 100 degrees Celsius for 8 hours.

After the reaction, the heating was stopped and 100 mL of ethyl acetate was added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 as the eluent and dried at 60 °C for 10 min. A yellow solid product (2-phenethyl) substituted fully substituted dithiooxamide compound was obtained in a yield of 100%.

The dithiooxamide compound obtained in this example is shown in Compound 5.

Example 6

Dodecyl-substituted dithiooxamide is prepared by the multi-component reaction of elemental sulfur, tetrachloroethane and amine compound to prepare dithiooxamide compound, and the reaction equation is shown in formula (VII):

The synthetic method steps are as follows:

In a reactor filled with argon, 8 mL of N,N-dimethylacetamide was dissolved in 8 mmol of dodecylamine, 2 mmol of tetrachloroethane and 10 mmol of sulfur, and heated to 100 degrees Celsius. Stir at 800 rpm for 8 hours.

After the reaction, the heating was stopped and 100 mL of ethyl acetate was added to quench and dilute the reaction solution, and then the solid precipitated in the reaction solution was removed by filtration. Using a saturated aqueous ammonium chloride solution as an aqueous phase and ethyl acetate as an organic phase, the solid-removed reaction solution was extracted, and the resulting organic phases were combined. The solvent of the combined organic phases was removed by evaporation under reduced pressure with heating and the crude product was obtained. Then, the purified product was separated from the system by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 4:1 as the eluent and dried at 60 °C for 10 min. The yield of dodecyl-substituted dithiooxamide compound was obtained as a black viscous solid product.

The dithiooxamide compound obtained in this example is shown in Compound 6.

It can be seen from the above examples that the present invention provides a dithiooxamide compound and a preparation method thereof, and the present invention realizes the N,N-dialiphatic group substituted dithiooxamide compound and N,N which are rarely reported. -The high-efficiency and low-cost preparation of diaryl-substituted dithiooxamide compounds, and the preparation method of the invention has the characteristics of mild reaction conditions, simple operation, diverse product structures, and the like.

The above are only the preferred embodiments of the present invention. It should be pointed out that for those skilled in the art, without departing from the principles of the present invention, several improvements and modifications can be made. It should be regarded as the protection scope of the present invention.

Claims (10)

1. a dithiooxamide compound, is characterized in that, described dithiooxamide compound comprises a kind of in following structural formula:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group; ^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group; R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent; R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents. 2. dithiooxamide compound according to claim 1, is characterized in that, described dithiooxamide compound specifically comprises a kind of in following structural formula:

3. the preparation method of the described dithiooxamide compound of claim 1 or 2, is characterized in that, comprises the following steps: The product obtained by the reaction of sulfur, tetrachloroethane and amine compounds is the dithiooxamide compound. 4 . The method for preparing a dithiooxamide compound according to claim 3 , wherein the molar ratio of the sulfur, tetrachloromethane and the amine compound is 0.25-10.0:0.17-4.0:1.0-10.0. 5 . 5. the preparation method of the dithiooxamide compound according to claim 3 or 4, is characterized in that, described amine compound comprises a kind of in following structural formula:

Wherein, R ¹ and R ² are independently aliphatic hydrocarbon groups, oxo aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents, oxo aliphatic hydrocarbon groups with aromatic substituents, aliphatic hydrocarbon groups with halogenated substituents or halogenated substituents oxo aliphatic hydrocarbon group; ^R3 and ^R4 are independently a hydrogen atom, a hydrocarbyl group, an alkoxy group, a halogen, a hydroxyl group, an ester group, a carbonyl group, an aryl group or a cyano group; R ⁵ and R ⁶ are independently a hydrocarbon group connected to nitrogen atoms on both sides at the same time, a hydrocarbon group with an aromatic substituent or a hydrocarbon group with a halogen substituent; R ⁷ and R ⁸ are independently aliphatic hydrocarbon groups, aliphatic hydrocarbon groups with aromatic substituents or aliphatic hydrocarbon groups with halogen substituents. 6. the preparation method of dithiooxamide compound according to claim 5, is characterized in that, described amine compound specifically comprises a kind of in following structural formula:

Here, n and k are independently an integer of 1-30. 7 . The method for preparing a dithiooxamide compound according to claim 6 , wherein the reaction is carried out in a solvent, and the molar volume ratio of the amine compound to the solvent is 0.01 to 5 mol: 1 L; 7 . The solvent contains one or more of N,N-dimethylformamide, N,N-dimethylacetamide and dimethylsulfoxide. 8 . The method for preparing a dithiooxamide compound according to claim 4 , wherein the reaction is carried out under a protective atmosphere, and the protective atmosphere contains nitrogen and/or argon. 9 . 9 . The method for preparing a dithiooxamide compound according to claim 8 , wherein the reaction temperature is 20-120° C., and the reaction time is 2-48 h. 10 . 10. The method for preparing a dithiooxamide compound according to claim 3 or 9, wherein the reaction is carried out under the action of a catalyst, and the catalyst is a basic compound, and the basic compound comprises N , one or more of N-diisopropylethylamine, triethylamine, potassium fluoride and potassium carbonate; the molar ratio of the catalyst and the amine compound is 10-40:1-10.

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