CN106699579A - Synthesis method of benzocaine - Google Patents
Synthesis method of benzocaine Download PDFInfo
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- CN106699579A CN106699579A CN201611016371.4A CN201611016371A CN106699579A CN 106699579 A CN106699579 A CN 106699579A CN 201611016371 A CN201611016371 A CN 201611016371A CN 106699579 A CN106699579 A CN 106699579A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Relating to the field of chemical engineering, the invention in particular relates to a synthesis method of benzocaine. The method includes the steps of: synthesis of p-nitrobenzoic acid; synthesis of ethyl 4-nitrobenzoate; and synthesis of benzocaine. Through improvement of benzocaine synthetic experiment method, the invention specifically solves the problems of low yield, tedious reaction aftertreatment and the like in conventional preparation experiments, and the improved experimental operation method not only can achieve high yield preparation of benzocaine, enhance experimental efficiency, but also effectively improves the teaching effects of the experimental course, and is suitable for chemical experimental course teaching.
Description
Technical field
The present invention relates to chemical field, and in particular to benzocainum synthetic method.
Background technology
Benzocainum (Benzocaine) is the popular name of ethylaminobenzoate, can be used as local anesthetic, benzene assistant
Cacaine is white crystalline powder, meets light color and gradually turns yellow, and the synthetic route of benzocainum may be summarized to be following 2 kinds：(1)
To be raw material to methylbenzene glue, benzocainum is obtained through acylation, oxidation, hydrolysis, esterification；(2) first reduced to nitre with ferrous sulfate
Yl benzoic acid obtains p-aminobenzoic acid, then is esterified to obtain benzocainum in acid condition with absolute ethyl alcohol.In the above method, method
(1) complex steps, cost of material is high, and discomfort a surname opens up student experimenting；Method (2) ferrous sulfate reduction generation is to amino
Benzoic acid, because the carbonyl in its product easily forms indissoluble salt with iron ion, is not readily separated, and is not suitable for education activities.
The content of the invention
In order to solve the above problems, the present invention provides a kind of raw material and is easy to get, and step is reasonable, it is easy to operate, and yield is higher, and
Benzocainum synthetic method suitable for education activities.
Benzocainum synthetic method of the present invention, comprises the following steps：
The first step, the synthesis of paranitrobenzoic acid in 250mL three-neck flasks, adds the para-nitrotoluene of 0.05mol and relative
It is 5% 4 bromide and 50mL distilled water in the molar fraction of para-nitrotoluene, reflux condensing tube, thermometer, stirring is installed
Device, opens stirring, after temperature is increased to 90 degree, is dividedly in some parts 0.125 mo1 KMnO4, reaction temperature is 90-95 degree,
Stirring reaction 2.5 hours；
Second step, room temperature is cooled to by reaction solution, filters out solid, and filter cake hot wash 2 times, filtrate merges, is acidified to
PH=2-3, separates out solid, filtering, cold water washing filter cake, through dry pale yellow crystals paranitrobenzoic acid；
3rd step, the synthesis of ethyl p-nitrobenzoate adds 0.015 in single neck round-bottom flask of dry 100 mL
Mo1 paranitrobenzoic acids, 25mL absolute ethyl alcohols, the 2.5mL concentrated sulfuric acids, the heating stirring back flow reaction 1.5h in water-bath will be anti-
Answer liquid to pour into the beaker equipped with 100mL frozen water, separate out crystal, suction filtration, filter cake is transferred in small beaker after washing 2 times with water, add
10 mL water soak, and it is 5% sodium carbonate solution that mass fraction is added under agitation, and regulation pH value of solution obtains faint yellow solid pair to 8
Ethyl nitrobenzoate；
4th step, the synthesis of benzocainum adds 1.95 grams of ethyl p-nitrobenzoates and 100mL in 250mL round-bottomed flasks
The solution that ethanol is made, adds 0.02 gram of Pd/C catalyst, is passed through hydrogen stirring reaction, and TLC monitoring reaction is tied until reaction
Beam, uses diatomite Filtration of catalyst, is spin-dried for removing ethanol, obtains final product white ethylaminobenzoate.
The present invention is improved by benzocainum compound experiment method, pointedly in the conventional preparation experiment of solution
Low yield, the problems such as post-reaction treatment is cumbersome, improved Examination on experimental operation not only can prepare benzene assistant card with high yield
Cause, improves conventional efficient, effectively improves the teaching efficiency of the laboratory, is suitable for Chemical Experiment Curriculum teaching.
Specific embodiment
Benzocainum synthetic method of the present invention, comprises the following steps：
The first step, the synthesis of paranitrobenzoic acid in 250mL three-neck flasks, adds the para-nitrotoluene of 0.05mol and relative
It is 5% 4 bromide and 50mL distilled water in the molar fraction of para-nitrotoluene, reflux condensing tube, thermometer, stirring is installed
Device, opens stirring, after temperature is increased to 90 degree, is dividedly in some parts 0.125 mo1 KMnO4, reaction temperature is 90-95 degree,
Stirring reaction 2.5 hours；
Second step, room temperature is cooled to by reaction solution, filters out solid, and filter cake hot wash 2 times, filtrate merges, is acidified to
PH=2-3, separates out solid, filtering, cold water washing filter cake, through dry pale yellow crystals paranitrobenzoic acid；
3rd step, the synthesis of ethyl p-nitrobenzoate adds 0.015 in single neck round-bottom flask of dry 100 mL
Mo1 paranitrobenzoic acids, 25mL absolute ethyl alcohols, the 2.5mL concentrated sulfuric acids, the heating stirring back flow reaction 1.5h in water-bath will be anti-
Answer liquid to pour into the beaker equipped with 100mL frozen water, separate out crystal, suction filtration, filter cake is transferred in small beaker after washing 2 times with water, add
10 mL water soak, and it is 5% sodium carbonate solution that mass fraction is added under agitation, and regulation pH value of solution obtains faint yellow solid pair to 8
Ethyl nitrobenzoate；
4th step, the synthesis of benzocainum adds 1.95 grams of ethyl p-nitrobenzoates and 100mL in 250mL round-bottomed flasks
The solution that ethanol is made, adds 0.02 gram of Pd/C catalyst, is passed through hydrogen stirring reaction, and TLC monitoring reaction is tied until reaction
Beam, uses diatomite Filtration of catalyst, is spin-dried for removing ethanol, obtains final product white ethylaminobenzoate.
The present invention is improved by benzocainum compound experiment method, pointedly in the conventional preparation experiment of solution
Low yield, the problems such as post-reaction treatment is cumbersome, improved Examination on experimental operation not only can prepare benzene assistant card with high yield
Cause, improves conventional efficient, effectively improves the teaching efficiency of the laboratory, is suitable for Chemical Experiment Curriculum teaching.
Claims (1)
1. a kind of benzocainum synthetic method, it is characterised in that comprise the following steps：
The first step, the synthesis of paranitrobenzoic acid in 250mL three-neck flasks, adds the para-nitrotoluene of 0.05mol and relative
It is 5% 4 bromide and 50mL distilled water in the molar fraction of para-nitrotoluene, reflux condensing tube, thermometer, stirring is installed
Device, opens stirring, after temperature is increased to 90 degree, is dividedly in some parts 0.125 mo1 KMnO4, reaction temperature is 90-95 degree,
Stirring reaction 2.5 hours；
Second step, room temperature is cooled to by reaction solution, filters out solid, and filter cake hot wash 2 times, filtrate merges, is acidified to
PH=2-3, separates out solid, filtering, cold water washing filter cake, through dry pale yellow crystals paranitrobenzoic acid；
3rd step, the synthesis of ethyl p-nitrobenzoate adds 0.015 in single neck round-bottom flask of dry 100 mL
Mo1 paranitrobenzoic acids, 25mL absolute ethyl alcohols, the 2.5mL concentrated sulfuric acids, the heating stirring back flow reaction 1.5h in water-bath will be anti-
Answer liquid to pour into the beaker equipped with 100mL frozen water, separate out crystal, suction filtration, filter cake is transferred in small beaker after washing 2 times with water, add
10 mL water soak, and it is 5% sodium carbonate solution that mass fraction is added under agitation, and regulation pH value of solution obtains faint yellow solid pair to 8
Ethyl nitrobenzoate；
4th step, the synthesis of benzocainum adds 1.95 grams of ethyl p-nitrobenzoates and 100mL in 250mL round-bottomed flasks
The solution that ethanol is made, adds 0.02 gram of Pd/C catalyst, is passed through hydrogen stirring reaction, and TLC monitoring reaction is tied until reaction
Beam, uses diatomite Filtration of catalyst, is spin-dried for removing ethanol, obtains final product white ethylaminobenzoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611016371.4A CN106699579A (en) | 2016-11-18 | 2016-11-18 | Synthesis method of benzocaine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611016371.4A CN106699579A (en) | 2016-11-18 | 2016-11-18 | Synthesis method of benzocaine |
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| CN106699579A true CN106699579A (en) | 2017-05-24 |
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| CN201611016371.4A Pending CN106699579A (en) | 2016-11-18 | 2016-11-18 | Synthesis method of benzocaine |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314627A (en) * | 2018-04-26 | 2018-07-24 | 常州永和精细化学有限公司 | Benzocainum green preparation process |
| CN111732521A (en) * | 2020-06-16 | 2020-10-02 | 浙江优创材料科技股份有限公司 | Preparation method of ethyl p-aminobenzoate |
| CN112526027A (en) * | 2020-12-10 | 2021-03-19 | 南京斯泰尔医药科技有限公司 | RT-HPLC detection method for benzocaine related substances |
-
2016
- 2016-11-18 CN CN201611016371.4A patent/CN106699579A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108314627A (en) * | 2018-04-26 | 2018-07-24 | 常州永和精细化学有限公司 | Benzocainum green preparation process |
| CN111732521A (en) * | 2020-06-16 | 2020-10-02 | 浙江优创材料科技股份有限公司 | Preparation method of ethyl p-aminobenzoate |
| CN111732521B (en) * | 2020-06-16 | 2021-04-20 | 浙江优创材料科技股份有限公司 | Preparation method of ethyl p-aminobenzoate |
| CN112526027A (en) * | 2020-12-10 | 2021-03-19 | 南京斯泰尔医药科技有限公司 | RT-HPLC detection method for benzocaine related substances |
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| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170524 |
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| WD01 | Invention patent application deemed withdrawn after publication |