CN108911989A - A kind of synthetic method of 2- methyl-3-trifluoromethyl phenylamine - Google Patents
A kind of synthetic method of 2- methyl-3-trifluoromethyl phenylamine Download PDFInfo
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Abstract
The invention discloses a kind of synthetic methods of 2- methyl-3-trifluoromethyl phenylamine, this method is using the chloro- 3- 5-trifluoromethylaniline of 2- as raw material, by introducing methyl mercapto on the chloro- 3- 5-trifluoromethylaniline of 2-, reacting that methyl mercapto is converted to chloromethyl and is neutralized again with sulfonic acid chloride adds the mode of hydrogen to obtain sterling 2- methyl-3-trifluoromethyl phenylamine, and synthetic route is
Description
Technical field
The present invention relates to the synthesis fields of compound, and in particular to one kind is closed using the chloro- 3- 5-trifluoromethylaniline of 2- as raw material
At the synthetic method of 2- methyl-3-trifluoromethyl phenylamine.
Background technique
2- methyl-3-trifluoromethyl phenylamine (2-Methyl-3-Trifluoromethyl Aniline) is a kind of important
Medicine, pesticide intermediate, be mainly used for synthesizing antalgica and herbicide and anti-inflammatory agent for animals etc., and synthesis Flunixin
The key intermediate of meglumine.Since the mutual position of 2- methyl-3-trifluoromethyl phenylamine benzene ring substituents is unique, synthesis
The process is more complicated, and production cost is higher.The chloro- 3- 5-trifluoromethylaniline synthetic method of the 2- disclosed in the prior art has one
Fixed drawback.
United States Patent (USP) US 5965735 disclose it is a kind of using mamino-trifluoromethyl benzene as the synthetic route of starting material, first will
Amino is reacted with pivaloyl chloride, and obtained amide is carried out with butyl lithium and iodomethane or dimethyl suflfate under cryogenic
Synthetic reaction obtains methylate, finally sloughs protecting group and obtains target product, and the amount for the butyl lithium that this route is used is big
In 2 equivalents, costly, while the iodomethane and dimethyl suflfate toxicity used are also larger for butyl lithium price, and methylation reaction needs
It to carry out under cryogenic, in view of conditions above, this route is not suitable for a large amount of industrial production demands, and synthetic route is as follows：
Chinese patent CN 103570558 discloses a kind of using 3- amino -4- chlorobenzotrifluoride as the synthesis road of starting material
Line protects amino with isobutyryl chloride, is methylated with butyl lithium and dimethyl suflfate, slough the chlorine on phenyl ring, be deprotected
To target product, there is document report that can also protect amino with pivaloyl chloride, the same isobutyryl chloride of remaining method, route is used
Synthetic method with mamino-trifluoromethyl benzene without significant difference, therefore, which is also not suitable for the need of a large amount of industrialized productions
It wants, synthetic route is as follows：
There is also a kind of in the prior art using 2- dichloromethyl benzotrifluoride as the synthetic method of starting material, by with chlorine
And Iod R, intermediate 2- dichloromethyl -5- chlorobenzotrifluoride is obtained, dichloromethyl is converted into methyl, obtained by yield 62%
To intermediate 2- methyl-5-chloro benzotrifluoride, nitration reaction, then dechlorination are then carried out, reduction nitro obtains target product.The road
The experimentation of line is cumbersome, and industrialized operability is poor, is not suitable as industrialized route and is developed, synthetic route
It is as follows：
Chinese patent CN 102491906 discloses a kind of side that target product is synthesized using 2-aminotoluene as starting material
Method, by two step fluorination reactions, with 4:1 ratio obtains the isomer of target product and target product.The route includes
Two step fluorination reactions, require consersion unit high, while obtained product is mixture, product isolate and purify difficulty compared with
Greatly, therefore the route also should not be used in industrialized production, and synthetic route is as follows：
Summary of the invention
In order to solve problem above, it is low suitable for industrial production, economic cost that the present invention provides one kind, more conducively environmentally friendly
The synthetic schemes of 2- methyl-3-trifluoromethyl phenylamine.2- methyl-3-trifluoromethyl phenylamine prepared by the present invention, preparation process letter
It is single, there is no toxic agent addition in preparation process, generated without toxicant yet, preparation process is simple and purity is higher.
To achieve the above object, the present invention uses following technical scheme：
A kind of synthetic method of 2- methyl-3-trifluoromethyl phenylamine, includes the following steps：
1. the synthesis of reaction intermediate I：
The chloro- 3- 5-trifluoromethylaniline of 2- is weighed, solvent is added, dimethyl sulphide, N- chlorine is added into system after mixing evenly
For succinimide, control is added speed, so that system temperature is maintained at lower temperature, add rear system and stir at room temperature
For a period of time, triethylamine is added in backward system, continues to be heated to reflux, cools down, water is added, liquid separation, sloughing will be residual after solvent
It stays object to be evaporated under reduced pressure, obtains reaction intermediate I.
Preferably, the chloro- 3- 5-trifluoromethylaniline of 2- is weighed, solvent is added, dimethyl sulfide is added into system after mixing evenly
Ether, N-chlorosuccinimide, control reaction temperature are no more than 30 DEG C, add rear system and stir 6-10h at room temperature, into
One step is preferred, is 6h.Backward system in triethylamine is added, continue to be heated to reflux 10h, cool down, water is added, liquid separation sloughs
Residue is evaporated under reduced pressure after solvent, obtains reaction intermediate I.
Above-mentioned solvent can be dichloroethanes, methylene chloride or toluene, preferably dichloroethanes.
Preferably, the chloro- 3- 5-trifluoromethylaniline of 2- in step 1：Solvent：Dimethyl sulphide：N-chlorosuccinimide：Three second
The mass ratio of amine is 1:(6-25):(0.3-0.65):(0.6-1.4):(0.5-1.55).
Preferably, the chloro- 3- 5-trifluoromethylaniline of 2- in step 1：Solvent：Dimethyl sulphide：N-chlorosuccinimide：Three second
The mass ratio of amine is 1:10:0.32:0.68:0.54.
2. the synthesis of reaction intermediate II：
Take in step 1 reaction intermediate I in reaction vessel, after dichloroethanes dissolution is added, under room temperature to system
Middle addition sulfonic acid chloride is passed through hydrogen chloride gas to solid into system and is completely dissolved after stirring, continue logical one section of hydrogen chloride gas
Time；It is filtered after system cooling, elutes filter cake with petroleum ether, obtain reaction intermediate II；
Preferably, reaction intermediate I obtained in step 1 is weighed in reaction vessel, and dichloroethanes, room temperature condition is added
It is lower that sulfonic acid chloride is added into system, after there is white solid in system, after continuing stirring 2-4 hours, it is preferred that be 2h；To
It is passed through hydrogen chloride gas to solid in system to be completely dissolved, continues logical 30min-1h, it is preferred that is 30min；System cooling, takes out
Filter, filter cake petroleum ether elution, obtains reaction intermediate II.
Preferably, reaction intermediate I in step 2：Dichloroethanes：The mass ratio of sulfonic acid chloride is 1:(5-13):(0.45-
0.8)。
Preferably, reaction intermediate I in step 2：Dichloroethanes：The mass ratio of sulfonic acid chloride is 1:6:0.53.
The synthesis of 3.2- methyl-3-trifluoromethyl phenylamine
It takes the reaction intermediate II in step 2 in pressure reaction still, ethyl alcohol, catalyst Pd/C, alkali is added；It is set with hydrogen
The air in system is changed, system reacts a period of time under the conditions of Hydrogen Vapor Pressure, cools down, and filters, sloughs solvent, residue is subtracted
Pressure distillation, obtains crystalline solid, i.e. 2- methyl-3-trifluoromethyl phenylamine.
Preferably, reaction intermediate II obtained in step 2 is weighed in pressure reaction still, and ethyl alcohol, catalyst Pd/ is added
C, alkali, selected alkali are triethylamine, sodium hydroxide, potassium hydroxide, lithium hydroxide, preferably sodium hydroxide.With in hydrogen displacement system
Air, system reacts 48-56h under the conditions of 4-6kg Hydrogen Vapor Pressure, it is preferred that reacts 48h under 4kg Hydrogen Vapor Pressure；Drop
Temperature filters, desolventizing, and residue vacuum distillation obtains crystalline solid, i.e. 2- methyl-3-trifluoromethyl phenylamine, synthetic route
It is as follows：
Preferably, reaction intermediate II in step 3：Ethyl alcohol：Catalyst Pd/C：The mass ratio of alkali is 1:(4-16):(0.1-
0.8):(0.3-0.9)。
Preferably, reaction intermediate II in step 3：Ethyl alcohol：Catalyst Pd/C：The mass ratio of alkali is 1:8:0.3:0.45.
Above-mentioned reaction intermediate I is the chloro- 2- of 6- (methyl mercapto) methyl-3-trifluoromethyl phenylamine, above-mentioned reaction intermediate II
For the chloro- 2- chloromethyl -3- trifluoromethylbenzene amine hydrochlorate of 6-.
Beneficial effects of the present invention
1. the present invention can high yield synthesis 2- methyl-3-trifluoromethyl phenylamine, it is raw materials used both economical, after reaction
By-product be easier to handle, environmental protection pressure is smaller, can be very good be applied to industrialized production.
2. synthetic route of the invention is also generated without noxious material, is answered in the synthesis process without introducing toxic reagent
It is safer for producing.
Specific embodiment
It is noted that following detailed description is all illustrative, it is intended to provide further instruction to the application.Unless another
It indicates, all technical and scientific terms used herein has usual with the application person of an ordinary skill in the technical field
The identical meanings of understanding.
Synthesis material used in the present embodiment is commercial product, and those skilled in the art can voluntarily buy.
Embodiment 1
1, the synthesis of the chloro- 2- of 6- (methyl mercapto) methyl-3-trifluoromethyl phenylamine：
The chloro- 3- 5-trifluoromethylaniline 606.2g of 2- is weighed, dichloroethanes 4L is added and is added after mixing evenly into system
Speed is added in dimethyl sulphide 280.2g, N-chlorosuccinimide, control, makes system temperature not higher than 30 degree, adds rear system
It stirs at room temperature and triethylamine 636g is added in 6 hours backward systems, system is heated to reflux, cool down, water is added, point
Liquid, desolventizing, residue vacuum distillation obtain product 635.8g yield 80%, and HPLC purity is greater than 97%.1H NMR
(600MHz,CDCl3) δ 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, the synthesis of the chloro- 2- chloromethyl -3- trifluoromethylbenzene amine hydrochlorate of 6-：
568.2g 6- chloro- 2- (methyl mercapto) methyl-3-trifluoromethyl phenylamine is weighed in reaction vessel, 4L dichloro is added
Ethane is added 278.3g sulfonic acid chloride into system under room temperature, white solid occurs in system, after continuing stirring 2 hours, to
It is passed through hydrogen chloride gas to solid in system to be completely dissolved, continues 30 minutes logical, system cooling, suction filtration, filter cake petroleum ether elutes,
Off-white powder 536g, yield 86% are obtained, HPLC purity is greater than 95%.1H NMR (600MHz, DMSO) δ 7.472 (d, J=
8.4Hz, 1H), 6.921 (d, J=8.4Hz, 1H), 4.855 (s, 2H)
3, the synthesis of 2- methyl-3-trifluoromethyl phenylamine
The chloro- 2- chloromethyl -3- trifluoromethylbenzene amine hydrochlorate 280g of 6- is weighed in pressure reaction still, ethyl alcohol is added, urges
Agent Pd/C, alkali.With the air in hydrogen displacement system, system is reacted 48 hours under the conditions of 4kg Hydrogen Vapor Pressure, is cooled down, and is taken out
Filter, desolventizing, residue vacuum distillation obtain crystalline solid 140g, yield 70%, and GC purity is greater than 99%, GC-MS (EI)
m/z 175。
Embodiment 2
1, the synthesis of the chloro- 2- of 6- (methyl mercapto) methyl-3-trifluoromethyl phenylamine：
The chloro- 3- 5-trifluoromethylaniline 1170g of 2- is weighed, dichloroethanes 17L is added and is added after mixing evenly into system
Speed is added in dimethyl sulphide 354g, N-chlorosuccinimide 961g, control, makes system temperature not higher than 30 degree, adds rear body
It ties up to stir under room temperature and triethylamine 1214g is added in 6 hours backward systems, system is heated to reflux, cool down, water is added,
Liquid separation, desolventizing, residue vacuum distillation obtain product 1193g yield 78%, and HPLC purity is greater than 95%.1H NMR
(600MHz,CDCl3) δ 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, the synthesis of the chloro- 2- chloromethyl -3- trifluoromethylbenzene amine hydrochlorate of 6-：
1020g 6- chloro- 2- (methyl mercapto) methyl-3-trifluoromethyl phenylamine is weighed in reaction vessel, bis- chloroethene of 8L is added
Alkane adds 810g sulfonic acid chloride into system, white solid occurs in system, under room temperature after continuing stirring 2 hours, into system
It is passed through hydrogen chloride gas to solid to be completely dissolved, continues 30 minutes logical, system cooling, suction filtration, the elution of filter cake petroleum ether obtains class
White solid 930g, yield 83%, HPLC purity are greater than 95%.1H NMR (600MHz, DMSO) δ 7.472 (d, J=8.4Hz,
1H), 6.921 (d, J=8.4Hz, 1H), 4.855 (s, 2H)
3, the synthesis of 2- methyl-3-trifluoromethyl phenylamine
The chloro- 2- chloromethyl -3- trifluoromethylbenzene amine hydrochlorate 560g of 6- is weighed in pressure reaction still, ethyl alcohol is added, urges
Agent Pd/C, alkali.With the air in hydrogen displacement system, system is reacted 48 hours under the conditions of 4kg Hydrogen Vapor Pressure, is cooled down, and is taken out
Filter, desolventizing, residue vacuum distillation obtain crystalline solid 262g, yield 75%, and GC purity is greater than 99%, GC-MS (EI)
m/z 175。
The foregoing is merely preferred embodiment of the present application, are not intended to limit this application, for the skill of this field
For art personnel, various changes and changes are possible in this application.Within the spirit and principles of this application, made any to repair
Change, equivalent replacement, improvement etc., should be included within the scope of protection of this application.
Claims (10)
1. a kind of synthetic method of 2- methyl-3-trifluoromethyl phenylamine, which is characterized in that steps are as follows：
(1) it takes the chloro- 3- 5-trifluoromethylaniline of 2- to be added in solvent, after mixing evenly, dimethyl sulphide, N- chloro is added into system
Succinimide, control reaction system are maintained at lower temperature, triethylamine are added into system after stirring at room temperature, heats back
Stream, after cooling plus water, residue is evaporated under reduced pressure after desolventizing, obtains reaction intermediate I by liquid separation；
(2) take in step (1) reaction intermediate I in reaction vessel, after dichloroethanes dissolution is added, under room temperature to system
Middle addition sulfonic acid chloride is passed through hydrogen chloride gas to solid into system and is completely dissolved after stirring, continue logical one section of hydrogen chloride gas
Time；It is filtered after system cooling, elutes filter cake with petroleum ether, obtain reaction intermediate II；
(3) it takes the reaction intermediate II in step (2) in pressure reaction still, ethyl alcohol, catalyst Pd/C, alkali is added；Use hydrogen
Air in displacement system, system react a period of time under the conditions of Hydrogen Vapor Pressure, cool down, and filter, solvent are sloughed, by residue
Vacuum distillation, obtains crystalline solid, i.e. 2- methyl-3-trifluoromethyl phenylamine.
2. synthetic method as described in claim 1, which is characterized in that the concrete operations of step (1) are as follows：Take the chloro- 3- tri- of 2-
Methyl fluoride aniline is added in solvent, after mixing evenly, dimethyl sulphide, N-chlorosuccinimide is added into system, control is anti-
It answers system temperature to be no more than 30 DEG C, triethylamine is added into system after stirring 6-10h at room temperature, is heated to reflux 10h, add after cooling
Residue is evaporated under reduced pressure after desolventizing, obtains reaction intermediate I by water, liquid separation；Preferably, at room temperature after stirring 6h to system
Middle addition triethylamine.
3. preparation method as claimed in claim 2, which is characterized in that the chloro- 3- 5-trifluoromethylaniline of 2-：Solvent：Diformazan
Thioether：N-chlorosuccinimide：The mass ratio of triethylamine is 1:(6-25):(0.3-0.65):(0.6-1.4):(0.5-
1.55)。
4. preparation method as claimed in claim 3, which is characterized in that the chloro- 3- 5-trifluoromethylaniline of 2-：Solvent：Diformazan
Thioether：N-chlorosuccinimide：The mass ratio of triethylamine is 1:10:0.32:0.68:0.54.
5. the preparation method as described in claim 1-4, which is characterized in that the solvent is dichloroethanes, methylene chloride or first
One of benzene.
6. synthetic method as described in claim 1, which is characterized in that the concrete operations of step (2) are as follows：It takes in step (1)
Reaction intermediate I after dichloroethanes dissolution is added, is added sulfonic acid chloride into system under room temperature, stirs in reaction vessel
Hydrogen chloride gas to solid is passed through in backward system to be completely dissolved, and continues logical hydrogen chloride gas 30min-1h；It is taken out after system cooling
Filter elutes filter cake with petroleum ether, obtains reaction intermediate II；Preferably, continue logical hydrogen chloride gas 30min.
7. synthetic method as claimed in claim 6, which is characterized in that reaction intermediate I in step (2)：Dichloroethanes：Sulphonyl
The mass ratio of chlorine is 1:(5-13):(0.45-0.8).
8. synthetic method as claimed in claim 7, which is characterized in that the reaction intermediate I：Dichloroethanes：Sulfonic acid chloride
Mass ratio is 1:6:0.53.
9. synthetic method as described in claim 1, which is characterized in that the concrete operations of step (3) are as follows：It takes in step (2)
Reaction intermediate II in pressure reaction still, be added ethyl alcohol, catalyst Pd/C, alkali；With the air in hydrogen displacement system, body
It ties up under the conditions of 4-6kg Hydrogen Vapor Pressure and reacts 48-56h, cool down, filter, slough solvent, residue is evaporated under reduced pressure, tied
Crystalline solid, i.e. 2- methyl-3-trifluoromethyl phenylamine；Preferably, reaction system reacts 48h under 4kg Hydrogen Vapor Pressure.
10. synthetic method as claimed in claim 9, which is characterized in that reaction intermediate II in step (3)：Ethyl alcohol：Catalyst
Pd/C：The mass ratio of alkali is 1:(4-16):(0.1-0.8):(0.3-0.9), it is preferred that be 1:8:0.3:0.45.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112394130A (en) * | 2020-12-02 | 2021-02-23 | 济南悟通生物科技有限公司 | Method for analyzing impurities in 2-methyl-3-trifluoromethylaniline synthesis process |
| CN114890902A (en) * | 2022-07-15 | 2022-08-12 | 和鼎（南京）医药技术有限公司 | Preparation method of 2-methyl-3-trifluoromethyl aniline |
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| CN112394130A (en) * | 2020-12-02 | 2021-02-23 | 济南悟通生物科技有限公司 | Method for analyzing impurities in 2-methyl-3-trifluoromethylaniline synthesis process |
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| CN114890902B (en) * | 2022-07-15 | 2022-09-27 | 和鼎（南京）医药技术有限公司 | Preparation method of 2-methyl-3-trifluoromethyl aniline |
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