CN109516919A - A kind of preparation method of three (2- amino-ethyl) amine - Google Patents
A kind of preparation method of three (2- amino-ethyl) amine Download PDFInfo
- Publication number
- CN109516919A CN109516919A CN201811607623.XA CN201811607623A CN109516919A CN 109516919 A CN109516919 A CN 109516919A CN 201811607623 A CN201811607623 A CN 201811607623A CN 109516919 A CN109516919 A CN 109516919A
- Authority
- CN
- China
- Prior art keywords
- amine
- amino
- ethyl
- preparation
- chloroethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation methods of three (2- amino-ethyl) amine, belong to technical field of compound preparation, it is using triethanolamine as starting material, triethanolamine and thionyl chloride and catalyst DMF are placed in reactor first, three (2- chloroethyl) amine hydrochlorates are generated under heating condition, then three (2- chloroethyl) amine hydrochlorates after purification organic solvent is dissolved in ammonium hydroxide to be placed in reactor, reaction obtains three (2- amino-ethyl) amine hydrochlorates in a heated condition, last three (2- amino-ethyl) amine hydrochlorate reacts to obtain three (2- amino-ethyl) amine with sodium hydroxide；Reaction route of the present invention is short, and controllability is stronger.
Description
Technical field
The present invention relates to technical field of compound preparation more particularly to a kind of synthetic technology of aliphatic nitrogen tritium tetramine to lead
Domain, specially a kind of preparation method of three (2- amino-ethyl) amine.
Background technique
Three (2- amino-ethyl) amine, structural formula are as follows:
Aliphatic nitrogen tritium tetramine can be used for the research such as chelating agent, corrosion inhibiter, resin curing agent, catalyst, organic intermediate
And industrial circle, three (2- amino-ethyl) amine are a kind of important organic polyamine chemical combination in aliphatic nitrogen tritium tetraamine compound
Object.Its nitrogen-atoms outstanding for being structurally characterized in that stronger coordination ability there are four tools in molecule, can be with most transition metal atoms
(such as Cd2+、Zn2+、Mn2+Deng) form the stable chelate with bicyclic ring structures.
In addition, to can be used for synthesizing phosphorous two rings organic nonionic superpower for the aliphatic nitrogen tritium tetramine such as three (2- amino-ethyl) amine
Alkali is the strongest proazaphosphatrane centered on phosphorus atoms found so far.As excellent base reagent or
Phosphorus ligand is employed successfully in many organic synthesis.But traditional synthesis technology there is only raw material more, behaviour at present
Make the disadvantages of cumbersome, yield is not high, and malicious byproduct harmful to human body and environment can be generated.
Summary of the invention
The present invention is intended to provide a kind of preparation method of three (2- amino-ethyl) amine, simple process, reaction is mild, environmental protection
Safety.
Used technical solution is as follows to solve above-mentioned technical problem by the present invention:
The present invention includes the following steps:
The preparation of (1) first intermediate: using triethanolamine and thionyl chloride as starting material, under the action of catalyst, add
Thermal response generates first intermediate three (2- chloroethyl) amine hydrochlorate；
The preparation of (2) second intermediates: first intermediate three (2- chloroethyl) amine hydrochlorate is isolated and purified, is dissolved in organic
In solvent, ammonium hydroxide is added thereto, reaction generates second intermediate three (2- amino-ethyl) amine hydrochlorate；
(3) preparation of target product: second intermediate three (2- amino-ethyl) amine hydrochlorate is isolated and purified, is added thereto
Strong base solution, adjust pH to 9-11, after fully reacting, obtain the reaction solution containing target product, by reaction solution isolate and purify to get
Three (2- amino-ethyl) amine.
As a further improvement of the present invention, catalyst is DMF in the step (1).
As a further improvement of the present invention, organic solvent is dehydrated alcohol in the step (2).
As a further improvement of the present invention, the strong base solution is sodium hydroxide solution.
As a further improvement of the present invention, the detailed process of the step (1) are as follows: by triethanolamine and DMF according to matter
Amount is placed in reactor than 1:1~2, thionyl chloride solution is slowly added dropwise while stirring, in 70 DEG C of temperature conditions after being added dropwise
Lower back flow reaction 6-8h is up to first intermediate three (2- chloroethyl) amine hydrochlorate.
As a further improvement of the present invention, the first intermediate three (2- chloroethyl) amine hydrochlorate isolates and purifies process
As follows: first intermediate three (2- chloroethyl) amine hydrochlorate that vacuum rotary steam generates removes remaining thionyl chloride solution, is used in combination
Dehydrated alcohol dissolves three (2- chloroethyl) amine hydrochlorates, and solid is precipitated after refrigeration, carries out suction filtration processing to solution after refrigeration, obtains
Second intermediate three (2- chloroethyl) amine hydrochlorate white crystal.
As a further improvement of the present invention, in the step (2) three (2- chloroethyl) amine hydrochlorates and ammonium hydroxide mole
Than for 1:10~40, reaction time 6-8h.
As a further improvement of the present invention, the second intermediate three (2- amino-ethyl) amine hydrochlorate isolated and purified
Journey is as follows: by reaction solution vacuum rotary steam obtained by step (2), removing remained ammonia, dehydrated alcohol dissolution is added, chlorine is precipitated after refrigeration
Change ammonium solid, filter, collects smoke filtrate, as three (2- amino-ethyl) amide hydrochlorides.
As a further improvement of the present invention, reaction solution is evaporated under reduced pressure, collects the fraction at 5kPa, 140-150 DEG C
As three (2- amino-ethyl) amine.
Synthetic route of the invention is as follows:
Compared with prior art, technical effect of the invention is as follows:
The present invention provides a kind of new methods for synthesizing three (2- amino-ethyl) amine to pass through three using triethanolamine as raw material
Footwork synthesizes three (2- amino-ethyl) amine, and each step reaction product is single, generates without excess byproduct, is convenient for separating-purifying,
It provides convenience for next step reaction, target product yield is higher, and synthetic route is succinct, and process flow is short, and selected raw material is honest and clean
Valence is easy to get, and production cost is low；Without a large amount of SO in the synthesis of three (2- chloroethyl) amine hydrochlorate intermediates of the invention2, HCl gas releases
It puts, reaction is mild, lower to human body and environmental hazard.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical scheme in the embodiment of the invention is clearly and completely described,
Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based in the present invention
Embodiment, every other embodiment obtained by those of ordinary skill in the art without making creative efforts, all
Belong to the scope of protection of the invention.
Embodiment 1:
45.45g triethanolamine solution is taken respectively, and 90gDMF is added in 1000ml three-necked flask, and stirring takes 150g protochloride
Sulfolane solution is slowly added dropwise into mentioned reagent, and rate of addition is controlled in 1 second every drop.Originally there is white solid and with gas
It generates, rear white solid disappearance, solution clarification is added dropwise.Continue stirring 7 hours.After completion of the reaction, vacuum rotary steam generates
Three (2- chloroethyl) amine hydrochlorates remove remaining thionyl chloride solution, and dissolve three (2- chloroethyls) with 300ml dehydrated alcohol
Solid is precipitated after refrigeration in amine hydrochlorate, carries out suction filtration processing to solution after refrigeration, obtains three (2- chloroethyl) amine hydrochlorates white
Crystal.
It takes 130g ammonium hydroxide to be added in 250ml three-necked flask, 48.2g above-mentioned three (2- chloroethyl) amine hydrochlorate is taken to be dissolved in
In 100g ethyl alcohol, stirring, and 70 DEG C of oil bath heating, keep solution to flow back, back flow reaction 7 hours.Reaction solution color by it is colourless by
Fade to dark brown.After completion of the reaction, revolving removes solvent and remaining ammonium hydroxide, obtains dark brown viscous object, takes 100ml anhydrous
Ethyl alcohol is dissolved, and chloride solid is precipitated after refrigeration, is filtered, and smoke filtrate is collected, and appropriate sodium hydroxide is added, and adjusting PH is 10
Left and right, reaction obtain three (2- amino-ethyl) amine, are evaporated under reduced pressure, and collecting the fraction at 5kp, 140~150 DEG C is three (2- ammonia
Base ethyl) amine.By weighing and calculating, three (2- amino-ethyl) amine yields 92.3%.
Embodiment 2:
75.75g triethanolamine solution is taken respectively, and 75gDMF is added in 1000ml three-necked flask, and stirring takes 250g protochloride
Sulfolane solution is slowly added dropwise into mentioned reagent, and rate of addition is controlled in 1 second every drop.Originally there is white solid and with gas
It generates, rear white solid disappearance, solution clarification is added dropwise.Continue stirring 7 hours.After completion of the reaction, vacuum rotary steam generates
Three (2- chloroethyl) amine hydrochlorates remove remaining thionyl chloride solution, and dissolve three (2- chloroethyls) with 500ml dehydrated alcohol
Solid is precipitated after refrigeration in amine hydrochlorate, carries out suction filtration processing to solution after refrigeration, obtains three (2- chloroethyl) amine hydrochlorates white
Crystal.
It takes 210g ammonium hydroxide to be added in 250ml three-necked flask, 48.2g above-mentioned three (2- chloroethyl) amine hydrochlorate is taken to be dissolved in
In 100g ethyl alcohol, stirring, and 70 DEG C of oil bath heating, keep solution to flow back, back flow reaction 7 hours.Reaction solution color by it is colourless by
Fade to dark brown.After completion of the reaction, revolving removes solvent and remaining ammonium hydroxide, obtains dark brown viscous object.Take 100ml anhydrous
Ethyl alcohol is dissolved, and chloride solid is precipitated after refrigeration, is filtered, and smoke filtrate is collected, and appropriate sodium hydroxide is added, and adjusting PH is 10
Left and right, reaction obtain three (2- amino-ethyl) amine, are evaporated under reduced pressure, and collecting the fraction at 5kp, 140~150 DEG C is three (2- ammonia
Base ethyl) amine.By weighing and calculating, the yield 82.24% of three (2- amino-ethyl) amine.
Embodiment 3:
60.6g triethanolamine solution is taken respectively, and 90gDMF is added in 1000ml three-necked flask, and stirring takes 200g protochloride
Sulfolane solution is slowly added dropwise into mentioned reagent, and rate of addition is controlled in 1 second every drop.Originally there is white solid and with gas
It generates, rear white solid disappearance, solution clarification is added dropwise.Continue stirring 7 hours.After completion of the reaction, vacuum rotary steam generates
Three (2- chloroethyl) amine hydrochlorates remove remaining thionyl chloride solution, and dissolve three (2- chloroethyls) with 500ml dehydrated alcohol
Solid is precipitated after refrigeration in amine hydrochlorate, carries out suction filtration processing to solution after refrigeration, obtains three (2- chloroethyl) amine hydrochlorates white
Crystal.
It takes 210g ammonium hydroxide to be added in 250ml three-necked flask, 48.2g above-mentioned three (2- chloroethyl) amine hydrochlorate is taken to be dissolved in
In 100g ethyl alcohol, stirring, and 70 DEG C of oil bath heating, keep solution to flow back, back flow reaction 7 hours.Reaction solution color by it is colourless by
Fade to dark brown.After completion of the reaction, revolving removes solvent and remaining ammonium hydroxide, obtains dark brown viscous object.Take 100ml anhydrous
Ethyl alcohol is dissolved, and chloride solid is precipitated after refrigeration, is filtered, and smoke filtrate is collected, and appropriate sodium hydroxide is added, and adjusting PH is 10
Left and right, reaction obtain three (2- amino-ethyl) amine, are evaporated under reduced pressure, and collecting the fraction at 5kp, 140~150 DEG C is three (2- ammonia
Base ethyl) amine.By weighing and calculating, the yield 84.80% of three (2- amino-ethyl) amine.
Embodiment described above is only that preferred embodiment of the invention is described, and is not carried out to the scope of the present invention
It limits, without departing from the spirit of the design of the present invention, those of ordinary skill in the art make technical solution of the present invention
Various changes and improvements, should all fall into claims of the present invention determine protection scope in.
Claims (9)
- The preparation method of one kind three 1. (2- amino-ethyl) amine, which comprises the steps of:The preparation of (1) first intermediate: using triethanolamine and thionyl chloride as starting material, under the action of catalyst, heating is anti- First intermediate three (2- chloroethyl) amine hydrochlorate should be generated；The preparation of (2) second intermediates: first intermediate three (2- chloroethyl) amine hydrochlorate is isolated and purified, organic solvent is dissolved in In, ammonium hydroxide is added thereto, reaction generates second intermediate three (2- amino-ethyl) amine hydrochlorate；(3) preparation of target product: second intermediate three (2- amino-ethyl) amine hydrochlorate isolates and purifies, and highly basic is added thereto Solution adjusts pH to 9-11, after fully reacting, obtains the reaction solution containing target product, reaction solution is isolated and purified to get three (2- amino-ethyl) amine.
- 2. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that the step (1) catalyst is DMF in.
- 3. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that the step (2) organic solvent is dehydrated alcohol in.
- 4. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that the highly basic is molten Liquid is sodium hydroxide solution.
- 5. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that the step (1) detailed process are as follows: triethanolamine and DMF are placed in reactor according to mass ratio 1:1~2, are slowly added dropwise while stirring Thionyl chloride solution flows reaction 6-8h next time in 70 DEG C of temperature conditions after being added dropwise up to the first intermediate three (2- chloroethyl) Amine hydrochlorate.
- 6. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that in described first It is as follows that mesosome three (2- chloroethyl) amine hydrochlorate isolates and purifies process: the first intermediate three (2- chloroethyl) that vacuum rotary steam generates Amine hydrochlorate removes remaining thionyl chloride solution, and dissolves three (2- chloroethyl) amine hydrochlorates with dehydrated alcohol, analyses after refrigeration Solid out carries out suction filtration processing to solution after refrigeration, obtains second intermediate three (2- chloroethyl) amine hydrochlorate white crystal.
- 7. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that the step (2) molar ratio of (2- chloroethyl) amine hydrochlorate and ammonium hydroxide is 1:10~40, reaction time 6-8h three in.
- 8. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that in described second It is as follows that mesosome three (2- amino-ethyl) amine hydrochlorate isolates and purifies process: reaction solution vacuum rotary steam obtained by step (2) removes surplus Remaining ammonium hydroxide is added dehydrated alcohol dissolution, chloride solid is precipitated after refrigeration, filter, collects smoke filtrate, as three (2- amino second Base) amide hydrochloride.
- 9. a kind of preparation method of three (2- amino-ethyl) amine according to claim 1, which is characterized in that subtract reaction solution Pressure distillation, the fraction collected at 5kPa, 140-150 DEG C is three (2- amino-ethyl) amine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811607623.XA CN109516919B (en) | 2018-12-27 | 2018-12-27 | Preparation method of tri (2-aminoethyl) amine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811607623.XA CN109516919B (en) | 2018-12-27 | 2018-12-27 | Preparation method of tri (2-aminoethyl) amine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109516919A true CN109516919A (en) | 2019-03-26 |
| CN109516919B CN109516919B (en) | 2021-12-14 |
Family
ID=65796979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811607623.XA Active CN109516919B (en) | 2018-12-27 | 2018-12-27 | Preparation method of tri (2-aminoethyl) amine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109516919B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438252A (en) * | 2018-12-27 | 2019-03-08 | 安徽工大化工科技有限公司 | A kind of synthesis technology of three (2- amino-ethyl) amine |
| CN109912428A (en) * | 2019-04-23 | 2019-06-21 | 长江大学 | N- is alkylated the preparation method of three amido star ultra-low molecular inhibitor |
| CN115448845A (en) * | 2022-10-22 | 2022-12-09 | 大连双硼医药化工有限公司 | Process method for synthesizing tri (2-aminoethyl) amine |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001187751A (en) * | 1999-12-28 | 2001-07-10 | Nippon Shokubai Co Ltd | New tren derivative and method for producing the same |
| WO2005007629A1 (en) * | 2003-07-16 | 2005-01-27 | Astrazeneca Ab | Piperidine or 8-aza-bicyclo[3.2.1]oct-3-yl derivatives useful as modulators of chemokine receptor activity |
| CN101678019A (en) * | 2007-06-08 | 2010-03-24 | 詹森药业有限公司 | piperidine/piperazine derivatives |
| CN103265677A (en) * | 2008-05-30 | 2013-08-28 | 东曹株式会社 | Process for producing hydroxyalkyltriethylenediamine compound, and catalyst composition for the production of polyurethane resin using the hydroxyalkyltriethylenediamine compound |
| CN104341333A (en) * | 2014-10-29 | 2015-02-11 | 北京华睿鼎信科技有限公司 | Preparation method of Pramiracetam sulfate |
| CN108084033A (en) * | 2017-12-29 | 2018-05-29 | 山东诚汇双达药业有限公司 | A kind of preparation method of N, N- diethyl ethylenediamine |
| CN109438252A (en) * | 2018-12-27 | 2019-03-08 | 安徽工大化工科技有限公司 | A kind of synthesis technology of three (2- amino-ethyl) amine |
-
2018
- 2018-12-27 CN CN201811607623.XA patent/CN109516919B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001187751A (en) * | 1999-12-28 | 2001-07-10 | Nippon Shokubai Co Ltd | New tren derivative and method for producing the same |
| WO2005007629A1 (en) * | 2003-07-16 | 2005-01-27 | Astrazeneca Ab | Piperidine or 8-aza-bicyclo[3.2.1]oct-3-yl derivatives useful as modulators of chemokine receptor activity |
| CN101678019A (en) * | 2007-06-08 | 2010-03-24 | 詹森药业有限公司 | piperidine/piperazine derivatives |
| CN103265677A (en) * | 2008-05-30 | 2013-08-28 | 东曹株式会社 | Process for producing hydroxyalkyltriethylenediamine compound, and catalyst composition for the production of polyurethane resin using the hydroxyalkyltriethylenediamine compound |
| CN104341333A (en) * | 2014-10-29 | 2015-02-11 | 北京华睿鼎信科技有限公司 | Preparation method of Pramiracetam sulfate |
| CN108084033A (en) * | 2017-12-29 | 2018-05-29 | 山东诚汇双达药业有限公司 | A kind of preparation method of N, N- diethyl ethylenediamine |
| CN109438252A (en) * | 2018-12-27 | 2019-03-08 | 安徽工大化工科技有限公司 | A kind of synthesis technology of three (2- amino-ethyl) amine |
Non-Patent Citations (3)
| Title |
|---|
| 吴伟，等: "三( 2-氨基乙基)胺合成方法的改进", 《化学试剂》 * |
| 樊有恒，等: "三(2-氨基乙基)胺盐酸盐的合成", 《化学试剂》 * |
| 陈金龙: "《精细有机合成原理与工艺》", 30 April 1992, 中国轻工业出版社 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438252A (en) * | 2018-12-27 | 2019-03-08 | 安徽工大化工科技有限公司 | A kind of synthesis technology of three (2- amino-ethyl) amine |
| CN109438252B (en) * | 2018-12-27 | 2021-12-14 | 安徽工业大学科技园有限公司 | Synthesis process of tri (2-aminoethyl) amine |
| CN109912428A (en) * | 2019-04-23 | 2019-06-21 | 长江大学 | N- is alkylated the preparation method of three amido star ultra-low molecular inhibitor |
| CN109912428B (en) * | 2019-04-23 | 2022-02-22 | 长江大学 | Preparation method of N-alkylated triamino star ultra-low molecular inhibitor |
| CN115448845A (en) * | 2022-10-22 | 2022-12-09 | 大连双硼医药化工有限公司 | Process method for synthesizing tri (2-aminoethyl) amine |
| CN115448845B (en) * | 2022-10-22 | 2024-05-03 | 大连双硼医药化工有限公司 | Process method for synthesizing tri (2-aminoethyl) amine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109516919B (en) | 2021-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106083922B (en) | A kind of preparation method of essence glufosinate-ammonium | |
| CN109516919A (en) | A kind of preparation method of three (2- amino-ethyl) amine | |
| CN109438252A (en) | A kind of synthesis technology of three (2- amino-ethyl) amine | |
| CA2724066C (en) | Method for producing bicyclic guanidines by use of a cyclic thiourea | |
| CN103360410A (en) | Preparation method of ofloxacin | |
| DK168069B1 (en) | ISOQUINOLINE DERIVATIVES AND A PROCEDURE FOR THE PREPARATION OF OCTAHYDROISOQUINOLINES FROM THE DERIVATIVES | |
| CN101412733B (en) | Preparation of N-alkyl thiophosphoryl triamide by one-pot method | |
| CN102617434B (en) | Process for preparing Vildagliptin by one-pot method | |
| CN101735827B (en) | Halogen-free aryl phosphonitrile fire retardant and preparation method thereof | |
| CN105017062A (en) | New method for preparing iopromide | |
| CN115947675A (en) | Rasagiline intermediate and preparation method and application thereof | |
| CN106946724A (en) | The synthetic method of the benzyl malonic acid mono ethyl ester of 2 acetylamino of monoamine base inhibitor class intermediate 2 | |
| CN108409557A (en) | Bu Waxitan new intermediates and its synthetic method and application | |
| CN103833660B (en) | The preparation method of lamotrigine and intermediate thereof | |
| CN107827886A (en) | A kind of refined preparation technology of high-purity AVM hereinafter Batan | |
| CN109206363A (en) | A kind of novel environment-friendly process preparing 2- chlorine apellagrin | |
| CN101607914A (en) | Simple method for preparing to tert-butyl benzyl amine | |
| WO2016202232A1 (en) | Synthesis method for (4s)-n-boc-4-methoxy methyl-l-proline amine salt | |
| JP5569938B2 (en) | Pyrrolidine derivative and method for producing the same | |
| CN113004248A (en) | Method for synthesizing carbazole compound by catalyzing hydrocarbon amination reaction with cobalt | |
| CN103145109A (en) | Method for preparing high-purity phosphorus pentafluoride and lithium hexafluorophosphate with organotin fluoride | |
| JP4711494B2 (en) | Method for producing thiobenzamides | |
| CN113845490B (en) | A preparation method of lisinopril intermediate | |
| CN109574778A (en) | A kind of preparation method of Bu Waxitan and its intermediate | |
| CN102603795A (en) | One-step Synthesis of Acephate from Phosphoryl Chloride |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20211125 Address after: 243000 scientific research building 1, Jiashan science and Technology Park, Ma'anshan economic and Technological Development Zone (Demonstration Park), Ma'anshan City, Anhui Province Applicant after: Anhui University of Technology Science Park Co.,Ltd. Address before: 238000 23 Xingguang Avenue, fine chemical industry base of He county, Ma'anshan City, Anhui Province Applicant before: ANHUI GONGDA CHEMICAL TECHNOLOGY CO.,LTD. |
|
| TA01 | Transfer of patent application right | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |