CN113845437B - Preparation method of amide derivative - Google Patents
Preparation method of amide derivative Download PDFInfo
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- CN113845437B CN113845437B CN202111322265.XA CN202111322265A CN113845437B CN 113845437 B CN113845437 B CN 113845437B CN 202111322265 A CN202111322265 A CN 202111322265A CN 113845437 B CN113845437 B CN 113845437B
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- 150000001408 amides Chemical class 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 238000006482 condensation reaction Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- -1 amine compound Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical group CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 3
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000005260 corrosion Methods 0.000 abstract description 2
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 108010008488 Glycylglycine Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Abstract
The invention relates to a preparation method of amide derivatives, and belongs to the technical field of organic synthesis. The preparation method of the amide derivative comprises the following steps: carrying out condensation reaction on a compound with a structure shown in a formula II and a compound shown in a formula III; the amide derivative has a structure shown in a formula I. The preparation method of the amide derivative has the advantages of simple process and low cost; the reaction condition is mild, and the equipment corrosion and the three wastes discharge can be reduced; easy operation, high production efficiency, improved utilization rate of equipment, more environment-friendly property and suitability for industrial mass production. The yield of the target product of the preparation method of the amide derivative is more than 80%.
Description
Technical Field
The invention relates to a preparation method of amide derivatives, and belongs to the technical field of organic synthesis.
Background
With the update and progress of technology, the extraction separation technology is widely applied to the fields of chemical medicines, foods, tobacco and spices, and is considered as the most promising collection method of noble metals and rare metals. The core of the extraction separation technology is an extracting agent, and the amide extracting agent is paid attention to because of the advantages of thorough combustion, good stability, no secondary pollution and the like, and can be used as the extracting agent in the extraction separation process of radioactive elements, actinides, lanthanide metals, rare earth metals, noble metals and the like.
N, N-di (2-ethylhexyl) -diglycolic acid is a novel amide extractant of nickel cobalt and rare noble metals, and has the structural formula:
Wherein R is-CH 2CH(CH2CH3)CH2CH2CH2CH3. The compound is hopeful to replace phosphoric acid extractant which is not easy to degrade in the market at present, and has wider market prospect.
In the prior art, yuan Xiaolan discloses a synthesis method of N, N-di (2-ethylhexyl) -diglycolamine (DEHDGA) and extraction behavior study of lanthanoid elements in the university of Nanhua 'Shuoshi's paper, which comprises the steps of synthesizing diglycolamine from left and right diglycol under the action of concentrated nitric acid, dehydrating diglycolamine to form diglycolamine, and generating a product with di (2-ethylhexyl) amine under an alkaline system. In the synthesis method, concentrated nitric acid is required to be used for reaction in the process of synthesizing the diglycine, and ammonia nitrogen discharged by the reaction is required to be absorbed by equipment, so that the process is complex, the operation environment is extremely unfriendly, and the equipment investment cost is high.
Disclosure of Invention
The invention aims to provide a preparation method of amide derivatives, which is simple in process and is beneficial to reducing production cost.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
A preparation method of amide derivatives comprises the following steps: carrying out condensation reaction on a compound with a structure shown in a formula II and a compound shown in a formula III; the amide derivative has a structure shown in a formula I;
In formula I and formula II, R 1、R2 is independently selected from C8-C10 alkyl;
In the formula I and the formula III, R 3 is methylene ethylene; in formula II, X is-Cl or-Br.
The preparation method of the amide derivative has the advantages of simple process and low cost; the reaction condition is mild, and the equipment corrosion and the three wastes discharge can be reduced; easy operation, high production efficiency, improved utilization rate of equipment, more environment-friendly property and suitability for industrial mass production. According to the preparation method of the amide derivative, the yield of the target product is more than 80%.
Preferably, the compound shown in the formula II and the compound shown in the formula III are subjected to the condensation reaction in a solvent under the action of an acid binding agent. The acid-binding agent used in the condensation reaction is preferably a basic compound. The basic compound is preferably an amine compound. The amine compound is preferably triethylamine. R 1 and R 2 may be the same C8-C10 alkyl group or different C8-C10 alkyl groups. C8-C10 alkyl is straight-chain alkyl or branched alkyl.
Preferably, the temperature of the condensation reaction is 10-70 ℃. The time of the condensation reaction is 6-16h. Specifically, the condensation reaction is to drop a compound II into a mixture of a compound of formula III, a solvent and an acid binding agent, stir the system after the drop is finished, and then perform the condensation reaction for 6-16h at the temperature of 10-70 ℃. The stirring time is 20-40min, for example 30min. Further, before dropping the compound of formula II, the temperature of the mixture is 60 ℃, and after stirring, the system is heated to 70 ℃ for condensation reaction.
Preferably, in formula I and formula II, R 1 and R 2 are both 2-ethylhexyl groups. The compound of the structure shown in the formula III is glycolic acid.
Preferably, the molar ratio of the compound of the structure shown in formula II to the compound of the structure shown in formula III is 1:2-4.
Preferably, the solvent used in the condensation reaction is an alcoholic solvent. The alcohol solvent is preferably methanol.
Preferably, the molar ratio of the alcohol solvent to the acid-binding agent used in the condensation reaction is 5-10:1.
When the solvent is an alcohol solvent and the acid binding agent is an amine compound, preferably, the preparation method of the amide derivative further comprises the following steps: and (3) distilling the system after the condensation reaction is finished to remove the alcohol solvent, then adding water for washing, then acidizing the organic phase, then washing with water, and finally distilling in vacuum to evaporate water and impurities. The acidification treatment is to add an acid, such as an inorganic acid, to the organic phase. The inorganic acid can be one or any combination of hydrochloric acid, sulfuric acid and nitric acid. The purpose of the acidification treatment is to remove trace alkaline substances in the alkaline system. The purity of the target product can reach more than 85% by adopting the subsequent treatment steps.
In the formula II, X is-Cl, and preferably, the compound shown in the formula II is obtained by performing chloroacetylation reaction on a compound with a structure shown in the formula IV and chloroacetyl chloride:
In formula IV, R 1、R2 is independently selected from C8-C10 alkyl.
The compound of formula IV is preferably diisooctylamine.
Preferably, the temperature of the chloroacetylation reaction is from 0 to 40 ℃, for example 28 ℃. The chloroacetylation reaction time is 2 to 10 hours, for example 6 hours.
Preferably, the molar ratio of the compound of formula IV to chloroacetyl chloride is 1:1-3, for example 1:1.3.
Preferably, the chloroacetylation reaction is carried out in a solvent under the action of an acid-binding agent. The acid-binding agent used in the chloroacetylation reaction is preferably a carbonate. The carbonate is sodium carbonate. The solvent adopted in the chloroacetylation reaction is water. Specifically, the preparation method of the compound of the formula IV comprises the following steps: dripping chloroacetyl chloride into a mixture of a compound shown in a formula IV, an acid binding agent and water, performing chloroacetylation reaction for 2-10 hours at 0-40 ℃ after dripping, separating out an organic phase after finishing the reaction, performing acidizing treatment on the obtained organic phase, washing with water, and distilling out water and low-boiling impurities to obtain the modified chloracetyl chloride. The dripping time of the chloroacetamide is 1h.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of an amide derivative prepared in example 1.
Detailed Description
The technical scheme of the invention is further described below with reference to the specific embodiments.
Example 1
The preparation method of the amide derivative comprises the following steps:
1) Adding sodium carbonate into a 100mL four-necked flask, adding water, stirring for dissolution, then adding 19.33g (0.08 mol) of diisooctylamine, stirring, dropwise adding 11.75g of chloroacetyl chloride at room temperature for 1 hour, controlling the temperature to react at 28 ℃ for 6 hours, then ending the reaction, separating out a water phase, adding 40mL of 10wt% hydrochloric acid into an organic phase for acidizing and washing treatment, and distilling out a small amount of water and low boiling point substances after water separation to obtain a product A;
weighing 24.26g, and calculating the yield of the product A to be more than 95.36%;
2) Then 11.41g of glycolic acid, 60mL of methanol and 15.18g of triethylamine are added into a 100mL four-necked flask, the temperature is raised to 60 ℃, 15.9g of A product is started to be added dropwise, the mixture is stirred for 30min after the completion of dropwise adding, and the mixture is heated to 70 ℃ for 16h to finish the reaction.
3) Distilling the reaction system obtained after the reaction in the step 2) to remove the alcohol solvent in the reaction system, then adding water for washing, adding 30mL of 10wt% hydrochloric acid into the organic phase for acidification after removing the water phase, washing with water, removing the water phase, and finally performing vacuum distillation to remove water and volatile substances to obtain the N, N-di (2-ethylhexyl) -diglycolic acid. In the second step of reaction, the yield of the amide derivative is more than 90%, and the purity of the product is more than 85%.
The amide derivatives prepared in this example were examined by nuclear magnetic resonance, and the results are shown in Table 1 and FIG. 1, which demonstrate that the final product was N, N-bis (2-ethylhexyl) -diglycolic acid.
TABLE 1 Hydrogen spectral data for N, N-bis (2-ethylhexyl) -diglycolic acid
| ΔH/ppm | Integration of | Number of hydrogen atoms | Peak type | Coupling constant J/Hz |
| 7.282-7.731 | 0.375 | 2 | s | |
| 4.031-4.150 | 0.375 | 2 | s | |
| 3.628-3.683 | 0.365 | 2 | d | 7.8 |
| 3.054-3.076 | 0.365 | 2 | d | 7.8 |
| 1.577-1.616 | 0.37 | 2 | m | |
| 1.256 | 3.0 | 16 | m | |
| 0.888 | 2.25 | 12 | m |
Example 2
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: the mass of chloroacetyl chloride added dropwise at room temperature in this example was 27g. The remaining non-descriptions are in full agreement with example 1. In the preparation method of the amide derivative of this example, the yield of the product A was 95.55%.
Example 3
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: in this example, after the completion of the addition of chloroacetyl chloride, the reaction was carried out at 0℃for 6 hours. The remaining non-descriptions are in full agreement with example 1. In the preparation method of the amide derivative of this example, the yield of the product A was 90.5%.
Example 4
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: in this example, after the completion of the addition of chloroacetyl chloride, the reaction was carried out at 28℃for 10 hours. The remaining non-descriptions are in full agreement with example 1. In the preparation method of the amide derivative of this example, the yield of the product A was 95.15%.
Example 5
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: the mass of glycolic acid used in this example was 15.21g, and the mass of triethylamine was 20.49g. The remaining non-descriptions are in full agreement with example 1. In the preparation method of the amide derivative, the final amide derivative has a yield of 89% and a purity of 84.8%.
Example 6
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: in the embodiment, after glycolic acid, methanol and triethylamine are added into a four-neck flask, the temperature is raised to 50 ℃ and then the product A is added dropwise; the remainder of the description is not exactly the same as in example 1.
In the preparation method of the amide derivative, the final amide derivative has a yield of 85% and a purity of 80%.
Example 7
The preparation method of the amide derivative of this example is different from the preparation method of the amide derivative of example 1 only in that: in step 2) of this example, the reaction time to raise the temperature to 70℃was 6 hours. The remainder of the description is not exactly the same as in example 1. In the preparation method of the amide derivative of the embodiment, the final yield of the amide derivative is 80%, and the purity reaches 83%.
Claims (7)
1. A preparation method of amide derivatives is characterized in that: the method comprises the following steps: carrying out condensation reaction on a compound with a structure shown in a formula II and a compound shown in a formula III; the amide derivative has a structure shown in a formula I;
In formula I and formula II, R 1、R2 is independently selected from C8-C10 alkyl;
in the formula I and the formula III, R 3 is methylene or ethylene; in the formula II, X is-Cl or-Br;
carrying out condensation reaction on a compound shown in a formula II and a compound shown in a formula III in a solvent under the action of an acid binding agent;
the solvent is an alcohol solvent; the alcohol solvent is methanol;
the method also comprises the following steps: distilling the system after the condensation reaction is finished to remove the alcohol solvent, then adding water for washing, then acidizing the organic phase, then washing with water, and finally distilling in vacuum to evaporate water and impurities; the acid binding agent is an amine compound; the acid binding agent is triethylamine.
2. The method for producing an amide derivative according to claim 1, wherein: the molar ratio of the alcohol solvent to the acid binding agent adopted in the condensation reaction is 5-10:1.
3. The method for producing an amide derivative according to claim 1, wherein: the temperature of the condensation reaction is 10-70 ℃, and the time of the condensation reaction is 6-16h.
4. The method for producing an amide derivative according to claim 1, wherein: in the formula I and the formula II, R 1 and R 2 are both 2-ethylhexyl, and the compound with the structure shown in the formula III is glycolic acid.
5. The method for producing an amide derivative according to claim 1, wherein: in the formula II, X is-Cl, and the compound shown in the formula II is obtained by performing chloracetyl reaction on a compound with a structure shown in the formula IV and chloracetyl chloride:
in formula IV, R 1、R2 is independently selected from C8-C10 alkyl.
6. The method for producing an amide derivative according to claim 5, wherein: the compound of formula IV is diisooctylamine.
7. The method for producing an amide derivative according to claim 5, wherein: the temperature of the chloracetyl reaction is 0-40 ℃; the time of the chloracetyl reaction is 2-10h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02104590A (en) * | 1987-06-15 | 1990-04-17 | Toyohiko Kikuchi | Production of antibiotic |
| JP2017095407A (en) * | 2015-11-25 | 2017-06-01 | 国立研究開発法人日本原子力研究開発機構 | Nitriloacetate diacetamide compound, extractant, and extraction method |
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- 2021-11-09 CN CN202111322265.XA patent/CN113845437B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02104590A (en) * | 1987-06-15 | 1990-04-17 | Toyohiko Kikuchi | Production of antibiotic |
| JP2017095407A (en) * | 2015-11-25 | 2017-06-01 | 国立研究開発法人日本原子力研究開発機構 | Nitriloacetate diacetamide compound, extractant, and extraction method |
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