Synthesis method of 1-(3, 5-bis (trifluoromethylphenyl)-3-cyclohexylthiourea
By employing a one-step synthesis method and purification steps, the problems of low yield and purity of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) were solved, achieving an efficient synthesis process and obtaining a high-purity product.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-09-27
- Publication Date
- 2026-03-27
AI Technical Summary
The existing synthesis methods for 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) have low yields and purity, which cannot meet the needs of practical applications.
A one-step synthesis method was used to react 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) with cyclohexylamine in a specific solvent, followed by purification treatment, including solvent removal and filter cake washing, to obtain a high-purity product.
The synthesis of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) with high yield and high purity was achieved, simplifying the operation process and improving product quality.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of chemical technology, specifically relating to a method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea). Background Technology
[0002] 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea is a chemical compound with specific physicochemical properties, including boiling point, density, and flash point, which are important for its application and safety assessment. Furthermore, this compound has a specific CAS number and English name, 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-(+)-2-(dimethylamino)cyclohexane]thiourea, and multiple aliases and English alternative names, reflecting its diversity and complexity in the chemical field. This compound is used as an intermediate in the synthesis of materials, demonstrating its important applications in chemical synthesis and materials science.
[0003] Currently, there is no practically applicable method for the synthesis of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), and the yield and purity are both relatively low. Summary of the Invention
[0004] To address the aforementioned technical problems, this invention provides a method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) that can be applied in practical applications and has high yield and high purity.
[0005] To solve this technical problem, the technical solution of the present invention is as follows: A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 1-isothiocyanate-3,5-bistrifluoromethylbenzene in a solvent, add cyclohexylamine at -1 to 2°C, heat to 28 to 36°C, react to obtain a mixed solution; (2) The mixture was purified to obtain 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea).
[0006] In some embodiments, the solvent in step (1) is dichloromethane.
[0007] In some embodiments, the ratio of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) to cyclohexylamine in step (1) is 25:9-13.
[0008] In some embodiments, purification in step (2) involves heating the mixture to remove half of the solvent, filtering, rinsing the filter cake with dichloromethane, and drying the filter cake.
[0009] In some embodiments, the reaction formula for the synthesis is as follows: . Beneficial effects
[0010] This invention utilizes a one-step synthesis method involving the reaction of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) with cyclohexylamine. This method is simple and easy to operate. Furthermore, the purification method employed in this invention can effectively improve both purity and yield. Detailed Implementation
[0011] Unless otherwise specified, all technical terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. In case of any discrepancy, the definitions in this specification shall prevail.
[0012] Unless otherwise stated, all percentages, portions, proportions, etc. are by weight.
[0013] The terms “comprising,” “including,” “having,” “containing,” “or any other variation thereof” as used herein are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to those elements, but may also include elements not expressly listed or other elements inherent to such composition, process, method, article, or apparatus.
[0014] When quantities, parts by weight, or other numerical values or parameters are given as ranges, preferred ranges, or a series of upper and lower preferred values, it should be understood that they specifically disclose all ranges formed by any pair of values of any larger or preferred range limit and any smaller or preferred range limit, regardless of whether the ranges are disclosed separately. For example, when describing a range of "1 to 5", the described range should be understood to include ranges such as "1 to 4", "1 to 3", "1 to 2", "1 to 2 and 4 to 5", "1 to 3 and 5", etc. Unless otherwise stated, where numerical ranges are described herein, the range is intended to include the range endpoints as well as all integers, fractions, decimals, etc., within that range.
[0015] Furthermore, the indefinite articles “a” and “an” preceding the elements or components of this disclosure are intended to indicate that there is no limitation on the number of times the said element or component appears (i.e., occurs). Therefore, “a” or “an” should be understood to include one or at least one, and unless the quantity is explicitly stated to be singular, the singular form of the said element or component also includes the plural case.
[0016] Unless otherwise specified, the materials, methods, and examples described herein are exemplary and not limiting. While similar or equivalent methods and materials may be used in implementing or testing this disclosure, suitable methods and materials are also described herein.
[0017] Yield calculation formula: (Product mass: Product molecular weight) / (Raw material mass: Raw material molecular weight).
[0018] This disclosure is described in detail below. Example 1
[0019] A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 9g of cyclohexylamine at -1℃, heat to 28℃, and react for 15h to obtain a mixed solution; (2) The mixture was purified by concentrating the mixture at 35°C to remove 100 mL of dichloromethane, filtering, washing the filter cake with dichloromethane (15 mL * 2), drying the filter cake, and obtaining 24.3 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea, with a yield of 71.2% and a purity of 97.6%. Example 2
[0020] A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 11g of cyclohexylamine at 0℃, heat to 31℃, and react for 15h to obtain a mixed solution. (2) The mixture was purified by concentrating the mixture at 35°C to remove 100 mL of dichloromethane, filtering, and washing the filter cake with dichloromethane (15 mL * 2). The filter cake was dried to obtain 26.4 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), with a yield of 77.3% and a purity of 98.2%. Example 3
[0021] A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 12g of cyclohexylamine at 0℃, heat to 33℃, and react for 15h to obtain a mixed solution. (2) The mixture was purified by concentrating the mixture at 35°C to remove 100 mL of dichloromethane, filtering, washing the filter cake with dichloromethane (15 mL * 2), drying the filter cake, and obtaining 27.8 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea, with a yield of 81.4% and a purity of 99.6%. Example 4
[0022] A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bistrifluoromethylbenzene in 200mL of dichloromethane, add 13g of cyclohexylamine at 2℃, raise the temperature to 36℃, and react for 15h to obtain a mixed solution; (2) The mixture was purified by concentrating the mixture at 35°C to remove 100 mL of dichloromethane, filtering, and washing the filter cake with dichloromethane (15 mL * 2). The filter cake was dried to obtain 20.8 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), with a yield of 60.9% and a purity of 95.4%.
[0023] Comparative Example 1 A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 12g of cyclohexylamine at 0℃, heat to 33℃, and react for 15h to obtain a mixed solution. (2) The mixture was purified by concentrating the mixture at 35°C to remove dichloromethane and drying it to obtain 28.1g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), with a yield of 82.3% and a purity of 92.9%.
[0024] Comparative Example 2 A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 12g of cyclohexylamine at 0℃, heat to 33℃, and react for 15h to obtain a mixed solution. (2) The mixture was purified by concentrating the mixture at 35°C to remove 80 mL of dichloromethane, filtering, washing the filter cake with dichloromethane (15 mL * 2), drying the filter cake, and obtaining 26.2 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea, with a yield of 76.7% and a purity of 96.7%.
[0025] Comparative Example 3 A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), the method comprising the following steps: (1) Dissolve 25g of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) in 200mL of dichloromethane, add 12g of cyclohexylamine at 0℃, heat to 33℃, and react for 15h to obtain a mixed solution. (2) The mixture was purified by concentrating the mixture at 35°C to remove 110 mL of dichloromethane, filtering, and washing the filter cake with dichloromethane (15 mL * 2). The filter cake was dried to obtain 26.9 g of 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), with a yield of 78.9% and a purity of 94.7%.
[0026] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.
Claims
1. A method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea), characterized in that, The synthesis method includes the following steps: (1) Dissolve 1-isothiocyanate-3,5-bistrifluoromethylbenzene in a solvent, add cyclohexylamine at -1 to 2°C, heat to 28 to 36°C, react to obtain a mixed solution; (2) The mixture was purified to obtain 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea).
2. The method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) according to claim 1, characterized in that, The solvent in step (1) is dichloromethane.
3. The method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) according to claim 2, characterized in that, In step (1), the ratio of 1-isothiocyanate-3,5-bis(trifluoromethylbenzene) to cyclohexylamine is 25:9-13.
4. The method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) according to claim 1, characterized in that, In step (2), purification involves heating the mixture to remove half of the solvent, filtering, rinsing the filter cake with dichloromethane, and drying the filter cake.
5. The method for synthesizing 1-(3,5-bis(trifluoromethylphenyl)-3-cyclohexylthiourea) according to claim 1, characterized in that, The reaction formula for this synthesis is: 。