CN108911989B - Synthesis method of 2-methyl-3-trifluoromethylaniline - Google Patents
Synthesis method of 2-methyl-3-trifluoromethylaniline Download PDFInfo
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- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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Abstract
The invention discloses a method for synthesizing 2-methyl-3-trifluoromethyl aniline, which takes 2-chloro-3-trifluoromethyl aniline as a raw material, introduces methylthio on the 2-chloro-3-trifluoromethyl aniline, reacts with sulfonyl chloride to convert the methylthio into chloromethyl, and then neutralizes and hydrogenates to obtain pure 2-methyl-3-trifluoromethyl aniline, and the synthetic route is that
Description
Technical Field
The invention relates to the field of compound synthesis, in particular to a synthesis method for synthesizing 2-methyl-3-trifluoromethyl aniline by using 2-chloro-3-trifluoromethyl aniline as a raw material.
Background
2-Methyl-3-Trifluoromethyl Aniline (2-Methyl-3-Trifluoromethyl Aniline) is an important intermediate of medicine and pesticide, is mainly used for synthesizing analgesic and herbicide, veterinary anti-inflammatory drug and the like, and is also a key intermediate for synthesizing flunixin meglumine. Because the mutual positions of the substituents on the benzene ring of the 2-methyl-3-trifluoromethyl aniline are unique, the synthesis process is more complex and the production cost is higher. The synthesis methods of 2-chloro-3-trifluoromethylaniline disclosed in the prior art have certain disadvantages.
U.S. Pat. No. 4, 5965735 discloses a synthetic route using m-amino benzotrifluoride as starting material, which comprises reacting amino group with pivaloyl chloride, reacting the obtained amide with butyl lithium and methyl iodide or dimethyl sulfate at low temperature to obtain methylated product, and removing protective group to obtain target product, wherein the amount of butyl lithium used in the route is more than 2 equivalents, the butyl lithium is expensive, the toxicity of the methyl iodide and dimethyl sulfate is high, and the methylation reaction needs to be carried out at low temperature, and the synthetic route is not suitable for mass industrial production due to the above conditions:
chinese patent CN 103570558 discloses a synthetic route using 3-amino-4-chlorotrifluoromethane as starting material, using isobutyryl chloride to protect amino, using butyl lithium and dimethyl sulfate to perform methylation, removing chlorine on benzene ring, and performing deprotection to obtain target product, and also using pivaloyl chloride to protect amino, and other methods are the same as isobutyryl chloride, and the synthetic method adopted by the route has no obvious difference from m-amino benzotrifluoride, therefore, the route is not suitable for the needs of mass industrial production, and the synthetic route is as follows:
in the prior art, a synthesis method using 2-dichloromethyl benzotrifluoride as an initial raw material is also available, and the intermediate 2-dichloromethyl-5-chlorotrifluoromethane is obtained by reacting with chlorine and iodine, wherein the yield is 62%, the dichloromethyl is converted into methyl to obtain the intermediate 2-methyl-5-chlorotrifluoromethane, and then the intermediate is subjected to nitration reaction, dechlorination and nitro reduction to obtain a target product. The experimental process of the route is complicated, the industrialized operability is poor, the route is not suitable for being developed as an industrialized route, and the synthetic route is as follows:
chinese patent CN 102491906 discloses a method for synthesizing a target product by using 2-methylaniline as a starting material, which obtains the target product and an isomer of the target product in a ratio of 4:1 through two-step fluorination reaction. The route comprises two steps of fluorination reaction, has high requirements on reaction equipment, and simultaneously obtains a mixture of products, and has higher separation and purification difficulty, so the route is not suitable for industrial production, and the synthetic route is as follows:
disclosure of Invention
In order to solve the problems, the invention provides a synthetic scheme of 2-methyl-3-trifluoromethyl aniline which is suitable for industrial production, has low economic cost and is more beneficial to environmental protection. The 2-methyl-3-trifluoromethyl aniline prepared by the invention has the advantages of simple preparation process, no toxic reagent added in the preparation process, no generation of toxic substances, simple preparation process and higher purity.
In order to achieve the purpose, the invention adopts the following technical scheme:
a synthetic method of 2-methyl-3-trifluoromethyl aniline comprises the following steps:
1. synthesis of reaction intermediate I:
weighing 2-chloro-3-trifluoromethylaniline, adding a solvent, uniformly stirring, adding dimethyl sulfide and N-chlorosuccinimide into a system, controlling the adding speed to keep the temperature of the system at a lower temperature, stirring the system for a period of time at room temperature after the addition is finished, adding triethylamine into the system, continuously heating and refluxing, cooling, adding water, separating liquid, removing the solvent, and then distilling the residue under reduced pressure to obtain a reaction intermediate I.
Preferably, weighing 2-chloro-3-trifluoromethylaniline, adding a solvent, uniformly stirring, adding dimethyl sulfide and N-chlorosuccinimide into the system, controlling the reaction temperature to be not more than 30 ℃, and stirring the system for 6-10 hours, more preferably 6 hours, at room temperature after the addition. And adding triethylamine into the system, continuously heating and refluxing for 10 hours, cooling, adding water, separating liquid, removing the solvent, and then distilling the residue under reduced pressure to obtain a reaction intermediate I.
The solvent may be dichloroethane, dichloromethane or toluene, preferably dichloroethane.
Preferably, the ratio of 2-chloro-3-trifluoromethylaniline in step 1: solvent: dimethyl sulfide: n-chlorosuccinimide: the weight ratio of triethylamine is 1 (6-25): (0.3-0.65): 0.6-1.4): 0.5-1.55.
Preferably, the ratio of 2-chloro-3-trifluoromethylaniline in step 1: solvent: dimethyl sulfide: n-chlorosuccinimide: the mass ratio of triethylamine is 1:10:0.32:0.68: 0.54.
2. Synthesis of reaction intermediate II:
putting the reaction intermediate I in the step 1 into a reaction container, adding dichloroethane for dissolving, adding sulfonyl chloride into the system at room temperature, stirring, introducing hydrogen chloride gas into the system until the solid is completely dissolved, and continuously introducing the hydrogen chloride gas for a period of time; after cooling, the system is filtered, and the filter cake is leached by petroleum ether to obtain a reaction intermediate II;
preferably, the reaction intermediate I obtained in the step 1 is weighed in a reaction container, dichloroethane is added, sulfonyl chloride is added into the system at room temperature, and after white solid appears in the system, the stirring is continued for 2 to 4 hours, preferably for 2 hours; introducing hydrogen chloride gas into the system until the solid is completely dissolved, and continuously introducing for 30min-1h, preferably 30 min; and cooling the system, performing suction filtration, and leaching a filter cake with petroleum ether to obtain a reaction intermediate II.
Preferably, the intermediate I is reacted in step 2: ethylene dichloride: the mass ratio of the sulfonyl chloride is 1 (5-13) to 0.45-0.8.
Preferably, the intermediate I is reacted in step 2: ethylene dichloride: the mass ratio of sulfonyl chloride is 1:6: 0.53.
Synthesis of 3.2-methyl-3-trifluoromethylaniline
Putting the reaction intermediate II obtained in the step 2 into a pressure reaction kettle, and adding ethanol, a catalyst Pd/C and alkali; replacing air in the system with hydrogen, reacting the system under the condition of hydrogen pressure for a period of time, cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain a crystalline solid, namely 2-methyl-3-trifluoromethylaniline.
Preferably, the reaction intermediate II obtained in the step 2 is weighed in a pressure reaction kettle, and ethanol, a catalyst Pd/C and alkali are added, wherein the alkali is selected from triethylamine, sodium hydroxide, potassium hydroxide and lithium hydroxide, and preferably sodium hydroxide. Replacing air in the system with hydrogen, and reacting the system for 48-56h under the condition of 4-6kg of hydrogen pressure, preferably reacting for 48h under the condition of 4kg of hydrogen pressure; cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain a crystalline solid, namely 2-methyl-3-trifluoromethylaniline, wherein the synthetic route is as follows:
preferably, step 3, intermediate II: ethanol: catalyst Pd/C: the mass ratio of the alkali is 1 (4-16) to (0.1-0.8) to (0.3-0.9).
Preferably, step 3, intermediate II: ethanol: catalyst Pd/C: the mass ratio of the alkali is 1:8:0.3: 0.45.
The reaction intermediate I is 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline, and the reaction intermediate II is 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride.
The invention has the advantages of
1. The method can synthesize the 2-methyl-3-trifluoromethyl aniline with high yield, the used raw materials are economic, the by-products after the reaction are easy to treat, the environmental protection pressure is low, and the method can be well applied to industrial production.
2. The synthetic route of the invention does not introduce toxic reagents in the synthetic process, does not generate toxic substances, and is safer when being applied to production.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
The synthetic raw materials used in the present examples are commercially available products, and can be purchased by those skilled in the art.
Example 1
1. Synthesis of 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline:
606.2g of 2-chloro-3-trifluoromethylaniline is weighed, 4L of dichloroethane is added, 280.2g of dimethyl sulfide and N-chlorosuccinimide are added into the system after uniform stirring, the adding speed is controlled, the temperature of the system is not higher than 30 ℃, 636g of triethylamine is added into the system after the system is stirred for 6 hours at room temperature after the addition is finished, the system is heated and refluxed, the temperature is reduced, water is added, liquid separation and solvent removal are carried out, and the residue is subjected to reduced pressure distillation to obtain 635.8g of a product, the yield is 80%, and the HPLC purity is higher than 97%.1H NMR(600MHz,CDCl3)7.304(d,J＝8.4Hz,1H),7.016(d,J＝8.4Hz,1H),5.2–4.7(br s,2H),3.885(s,2H),2.051(s,3H)
2. Synthesis of 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride:
568.2g of 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline is weighed into a reaction container, 4L of dichloroethane is added, 278.3g of sulfonyl chloride is added into the system at room temperature, white solid appears in the system, after stirring is continued for 2 hours, hydrogen chloride gas is introduced into the system until the solid is completely dissolved, introduction is continued for 30 minutes, the system is cooled, suction filtration is carried out, and petroleum ether is filtered to obtain 536g of white-like solid, wherein the yield is 86%, and the HPLC purity is higher than 95%.1H NMR(600MHz,DMSO)7.472(d,J＝8.4Hz,1H),6.921(d,J＝8.4Hz,1H),4.855(s,2H)
3. Synthesis of 2-methyl-3-trifluoromethylaniline
Weighing 280g of 6-chloro-2-chloromethyl-3-trifluoromethyl aniline hydrochloride into a pressure reaction kettle, and adding ethanol, a catalyst Pd/C and alkali. Replacing air in the system with hydrogen, reacting the system for 48 hours under the condition of 4kg of hydrogen pressure, cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain 140g of crystalline solid with the yield of 70 percent, the GC purity of more than 99 percent and GC-MS (EI) m/z 175.
Example 2
1. Synthesis of 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline:
weighing 1170g of 2-chloro-3-trifluoromethylaniline, adding 17L of dichloroethane, uniformly stirring, adding 354g of dimethyl sulfide and 961g of N-chlorosuccinimide into the system, controlling the adding speed to ensure that the temperature of the system is not higher than 30 ℃, stirring the system for 6 hours at room temperature after the addition is finished, adding 1214g of triethylamine into the system, heating and refluxing the system, cooling, adding water, separating, removing a solvent, and distilling residues under reduced pressure to obtain 1193g of a product with the yield of 78% and the HPLC purity of more than 95%.1H NMR(600MHz,CDCl3)7.304(d,J＝8.4Hz,1H),7.016(d,J＝8.4Hz,1H),5.2–4.7(br s,2H),3.885(s,2H),2.051(s,3H)
2. Synthesis of 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride:
weighing 1020g of 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline into a reaction container, adding 8L of dichloroethane, adding 810g of sulfonyl chloride into the system at room temperature, continuously stirring for 2 hours, introducing hydrogen chloride gas into the system until the solid is completely dissolved, continuously introducing for 30 minutes, cooling the system, carrying out suction filtration, leaching filter cake petroleum ether, and obtaining 930g of off-white solid, wherein the yield is 83%, and the HPLC purity is more than 95%.1H NMR(600MHz,DMSO)7.472(d,J＝8.4Hz,1H),6.921(d,J＝8.4Hz,1H),4.855(s,2H)
3. Synthesis of 2-methyl-3-trifluoromethylaniline
560g of 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride is weighed into a pressure reaction kettle, and ethanol, a catalyst Pd/C and alkali are added. Replacing air in the system with hydrogen, reacting the system for 48 hours under the condition of 4kg of hydrogen pressure, cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain 262g of crystalline solid, wherein the yield is 75%, the GC purity is more than 99%, and the GC-MS (EI) m/z 175 is obtained.
The above description is only a preferred embodiment of the present application and is not intended to limit the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (14)
1. A synthetic method of 2-methyl-3-trifluoromethyl aniline is characterized by comprising the following steps:
(1) adding 2-chloro-3-trifluoromethylaniline into a solvent, uniformly stirring, adding dimethyl sulfide and N-chlorosuccinimide into a system, controlling the reaction system to be kept at a lower temperature, stirring at room temperature, adding triethylamine into the system, heating and refluxing, cooling, adding water, separating, removing the solvent, and distilling the residue under reduced pressure to obtain a reaction intermediate I;
(2) putting the reaction intermediate I in the step (1) into a reaction container, adding dichloroethane for dissolving, adding sulfonyl chloride into the system at room temperature, stirring, introducing hydrogen chloride gas into the system until the solid is completely dissolved, and continuously introducing the hydrogen chloride gas for a period of time; after cooling, the system is filtered, and the filter cake is leached by petroleum ether to obtain a reaction intermediate II;
(3) putting the reaction intermediate II in the step (2) into a pressure reaction kettle, and adding ethanol, a catalyst Pd/C and alkali; replacing air in the system with hydrogen, reacting the system under the condition of hydrogen pressure for a period of time, cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain a crystalline solid, namely 2-methyl-3-trifluoromethylaniline;
the reaction intermediate I is 6-chloro-2- (methylthio) methyl-3-trifluoromethylaniline; the reaction intermediate II is 6-chloro-2-chloromethyl-3-trifluoromethylaniline hydrochloride.
2. The synthesis method according to claim 1, wherein the specific operation of step (1) is as follows: adding 2-chloro-3-trifluoromethylaniline into a solvent, uniformly stirring, adding dimethyl sulfide and N-chlorosuccinimide into a system, controlling the temperature of the reaction system to be not more than 30 ℃, stirring at room temperature for 6-10h, adding triethylamine into the system, heating and refluxing for 10h, cooling, adding water, separating, removing the solvent, and distilling the residue under reduced pressure to obtain a reaction intermediate I.
3. The synthesis method of claim 2, wherein triethylamine is added to the system after stirring for 6h at room temperature.
4. The method of synthesis according to claim 2, wherein the 2-chloro-3-trifluoromethylaniline: solvent: dimethyl sulfide: n-chlorosuccinimide: the mass ratio of the triethylamine is 1:6-25:0.3-0.65:0.6-1.4: 0.5-1.55.
5. The method of synthesis according to claim 4, wherein the 2-chloro-3-trifluoromethylaniline: solvent: dimethyl sulfide: n-chlorosuccinimide: the mass ratio of triethylamine is 1:10:0.32:0.68: 0.54.
6. The method of any one of claims 1-5, wherein the solvent is one of dichloroethane, dichloromethane, or toluene.
7. The synthesis method according to claim 1, wherein the specific operation of step (2) is as follows: putting the reaction intermediate I in the step (1) into a reaction container, adding dichloroethane for dissolving, adding sulfonyl chloride into the system at room temperature, stirring, introducing hydrogen chloride gas into the system until the solid is completely dissolved, and continuously introducing the hydrogen chloride gas for 30min-1 h; and (4) carrying out suction filtration after the system is cooled, and leaching the filter cake with petroleum ether to obtain a reaction intermediate II.
8. The method of synthesis according to claim 7, wherein the continuous introduction of hydrogen chloride gas is carried out for a period of 30 min.
9. The method of claim 7, wherein in step (2) intermediate I: ethylene dichloride: the mass ratio of the sulfonyl chloride is 1:5-13: 0.45-0.8.
10. The synthetic process of claim 9 wherein the reaction intermediate I: ethylene dichloride: the mass ratio of sulfonyl chloride is 1:6: 0.53.
11. The synthesis method according to claim 1, wherein the specific operation of step (3) is as follows: putting the reaction intermediate II in the step (2) into a pressure reaction kettle, and adding ethanol, a catalyst Pd/C and alkali; replacing air in the system with hydrogen, reacting the system for 48-56h under the condition of 4-6kg of hydrogen pressure, cooling, filtering, removing the solvent, and distilling the residue under reduced pressure to obtain a crystalline solid, namely the 2-methyl-3-trifluoromethylaniline.
12. The synthesis process according to claim 11, characterized in that the system is reacted for 48h under a pressure of 4kg of hydrogen.
13. The method of claim 11, wherein in step (3) intermediate II: ethanol: catalyst Pd/C: the mass ratio of the alkali is 1:4-16:0.1-0.8: 0.3-0.9.
14. The method of claim 11, wherein in step (3) intermediate II: ethanol: catalyst Pd/C: the mass ratio of the alkali is 1:8:0.3: 0.45.
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