EP4118068A1 - Method for preparing benzamide compound - Google Patents
Method for preparing benzamide compoundInfo
- Publication number
- EP4118068A1 EP4118068A1 EP21712120.1A EP21712120A EP4118068A1 EP 4118068 A1 EP4118068 A1 EP 4118068A1 EP 21712120 A EP21712120 A EP 21712120A EP 4118068 A1 EP4118068 A1 EP 4118068A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- solid
- reaction
- benzamide compound
- ion exchange
- exchange resin
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- -1 benzamide compound Chemical class 0.000 title claims abstract description 35
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims abstract description 34
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 32
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 32
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000002378 acidificating effect Effects 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 230000007062 hydrolysis Effects 0.000 claims abstract description 29
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 29
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 29
- ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical class C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 claims abstract description 26
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000011343 solid material Substances 0.000 claims description 19
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012265 solid product Substances 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005998 bromoethyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000011344 liquid material Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 24
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract description 9
- 239000002699 waste material Substances 0.000 abstract description 6
- 238000009776 industrial production Methods 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical group ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000005863 Zoxamide Substances 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- CLHMRPUZSGUHMI-UHFFFAOYSA-N CCC1(COC(=N1)C2=CC(=C(C(=C2)Cl)C)Cl)C Chemical compound CCC1(COC(=N1)C2=CC(=C(C(=C2)Cl)C)Cl)C CLHMRPUZSGUHMI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- JFCGHLOKPBHXDF-UHFFFAOYSA-N n-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC=C(C)C=C1 JFCGHLOKPBHXDF-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 241000233654 Oomycetes Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
Definitions
- the present invention relates to the technical field of organic synthesis, in particular to a method for preparing a benzamide compound.
- Benzamide compounds are a class of compounds with a wide range of uses, among them, many compounds have biological activities, such as antibacterial, fungicidal and herbicidal activities; such compounds have very low residual toxicity and are environmentally friendly, therefore they have a very broad application space in the agricultural field.
- Zoxamide is a microtubulin aggregation inhibitor that was developed and marketed by Rohm & Haas in the United States in 2001 for the prevention and control of oomycete pathogenic microorganisms, and its structural formula is as shown in formula a:
- An object of the present invention is to provide a method for preparing a benzamide compound, the method provided by the present invention relates to the use of p-toluenesulphonic acid or sulphonic acid ion exchange resin as an acidic catalyst to catalyze the hydrolysis ring opening reaction of the aryl-substituted dihydrooxazole to obtain the benzamide compound, only a catalytically metered toluenesulphonic acid or sulphonic acid ion exchange resin is needed, the toluenesulphonic acid or sulphonic acid ion exchange resin is convenient to remove after the reaction is completed, with very little waste, and industrial production is convenient to achieve.
- a method for preparing a benzamide compound comprising the following steps:
- the acidic catalyst is a p- toluenesulphonic acid or sulphonic acid ion exchange resin
- the aryl-substituted dihydrooxazole has a structure as shown in formula I: formula I;
- Ri, R2 and R3 are independently hydrogen, hydrocarbyl or substituted hydrocarbyl, and Xi, X2 and X3 are independently hydrogen or a halogen group.
- the numbers of the carbon atoms of the hydrocarbyl and the substituted hydrocarbyl are independently 1 to 5, and the halogen group includes -F, - Cl, -Br or -I.
- the hydrocarbyl includes methyl or ethyl; the substituted hydrocarbyl includes chloromethyl or bromoethyl.
- the reaction solvent includes one or more of ethanol, methanol, methyl tert-butyl ketone and methyl tert-butyl ether.
- the molar ratio of the aryl- substituted dihydrooxazole to p-toluenesulphonic acid is 1 : 0.01-0.5, and the mass of the sulphonic acid ion exchange resin is 1 to 5% of the mass of the aryl-substituted dihydrooxazole;
- the molar ratio of the aryl-substituted dihydrooxazole, water and reaction solvent is 1 : 1-1.5 : 1- 20.
- the temperature of the hydrolysis ring-opening reaction is 50 to 80°C, and the time is 2 to 10 h.
- the above mentioned method results in obtaining a product material solution comprising a precipitate which comprises the benzamide compound.
- the acidic catalyst is p-toluenesulphonic acid
- the method further comprises:
- the solvent used in the slurrying washing treatment includes one or more of ethanol, methyl tert-butyl ketone and toluene.
- the method further comprises:
- the temperature of the heating is 70 to 80°C.
- the present invention provides a method for preparing a benzamide compound comprising the following steps: mixing aryl-substituted dihydrooxazole, an acidic catalyst, water and a reaction solvent, and subjecting same to a hydrolysis ring-opening reaction to obtain the benzamide compound, wherein the acidic catalyst is a p- toluenesulphonic acid or sulphonic acid ion exchange resin.
- the acidic catalyst is a p- toluenesulphonic acid or sulphonic acid ion exchange resin.
- a p-toluenesulphonic acid or sulphonic acid ion exchange resin is used as an acidic catalyst.
- aryl-substituted dihydrooxazole is subjected to a hydrolysis ring-opening reaction to obtain the benzamide compound, only catalytically metered toluenesulphonic acid or sulphonic acid ion exchange resin is needed, the toluenesulphonic acid or sulphonic acid ion exchange resin is convenient to remove after the completion of the reaction, with very little waste, and industrial production is convenient to achieve.
- the method provided by the present invention has mild and controllable reaction conditions, a simple and convenient reaction post-treatment, without needing complicated purification operations, has a high product yield and a high purity, and has the advantages of being green and environmentally friendly.
- the present invention provides a method for preparing a benzamide compound comprising the following steps: [0029] mixing aryl-substituted dihydrooxazole, an acidic catalyst, water and a reaction solvent, and subjecting same to a hydrolysis ring-opening reaction to obtain the benzamide compound,
- the acidic catalyst is a p- toluenesulphonic acid or sulphonic acid ion exchange resin
- the aryl-substituted dihydrooxazole has a structure as shown in formula I:
- Ri, R 2 and R 3 are independently hydrogen, hydrocarbyl or substituted hydrocarbyl, and Xi, X 2 and X 3 are independently hydrogen or a halogen group.
- the numbers of the carbon atoms of the hydrocarbyl and the substituted hydrocarbyl are independently 1 to 5, more preferably, the hydrocarbyl includes methyl or ethyl; the substituted hydrocarbyl includes chloromethyl or bromoethyl; the halogen group preferably includes -F, -Cl, -Br or -I.
- the benzamide compound has a structure as shown in formula II: [0036] formula II;
- the aryl-substituted dihydrooxazole is subjected to a hydrolysis ring-opening reaction to obtain a benzamide compound; the reaction formula is as shown in formula a:
- aryl-substituted dihydrooxazole, an acidic catalyst, water and a reaction solvent are mixed to obtain a reaction solution.
- the acidic catalyst is a p- toluenesulphonic acid or sulphonic acid ion exchange resin.
- a p-toluenesulphonic acid or sulphonic acid ion exchange resin is used as an acidic catalyst.
- aryl-substituted dihydrooxazole is subjected to a hydrolysis ring-opening reaction to obtain the benzamide compound, only catalytically metered toluenesulphonic acid or sulphonic acid ion exchange resin is needed, the toluenesulphonic acid or sulphonic acid ion exchange resin is convenient to remove after the completion of the reaction, with very little waste, and industrial production is convenient to achieve.
- the reaction solvent preferably includes one or more of ethanol, methanol, methyl tert-butyl ketone and methyl tert-butyl ether, more preferably, ethanol and methyl tert-butyl ketone; in the embodiment of the present invention, anhydrous ethanol is specifically used as the reaction solvent.
- the molar ratio of the aryl-substituted dihydrooxazole to p-toluenesulphonic acid is preferably 1 : 0.01-0.5, more preferably 1 : 0.05- 0.1;
- the mass of the sulphonic acid ion exchange resin is preferably 1 to 5% of the mass of the aryl-substituted dihydrooxazole, more preferably 1 to 3%;
- the molar ratio of the aryl-substituted dihydrooxazole, water and reaction solvent is preferably 1 : 1-1.5 : 1-20, more preferably 1 : 1-1.2 : 5-10.
- the method of mixing the aryl-substituted dihydrooxazole, acidic catalyst, water and reaction solvent is not particularly limited, as long as they can be uniformly mixed.
- the temperature of the heating is preferably 45 to 80°C, more preferably 60 to 65°C, and the stirring time is preferably 5 to 15 min, more preferably 10 min; the present invention has no particular limitation on the stirring, as long as a conventional stirring rate is used.
- a hydrolysis ring opening- reaction is performed to obtain a benzamide compound.
- the temperature of the hydrolysis ring opening reaction is preferably 50 to 80°C, more preferably 60 to 65°C, and the time is preferably 2 to 10 h. Specifically, the reaction progress is monitored by chromatography.
- the aryl-substituted dihydrooxazole undergoes a hydrolysis ring-opening reaction to generate a benzamide compound.
- a white solid will gradually precipitate out of the system. When the white solid is completely precipitated, the hydrolysis ring-opening reaction is completed, and the white solid is the benzamide compound.
- the method when the acidic catalyst is p-toluenesulphonic acid, after the hydrolysis ring opening reaction, the method preferably further comprises:
- the solvent used in the slurrying washing treatment preferably includes one or more of ethanol, methyl tert-butyl ketone and toluene, more preferably ethanol or toluene.
- anhydrous ethanol is specifically used as the solvent.
- the present invention has no particular limitation on the amount of solvent and the specific method of the slurrying washing treatment, as long as the amount and method well known to those skilled in the art are used.
- the impurities in the first solid material are removed through the slurrying washing treatment to realize the purification thereof.
- the present invention has no particular limitation on the drying, as long as the product can be fully dried.
- the method when the acidic catalyst is a sulphonic acid ion exchange resin, after the hydrolysis ring-opening reaction, the method preferably further comprises:
- the present invention has no particular limitation on the amount of water used to dissolve the first solid material, as long as it can ensure that the first solid material is fully dissolved under the heating condition and facilitate the precipitation of the solid products by subsequent cooling.
- the temperature of the heating is preferably from 70 to 80°C.
- the present invention has no particular limitation on the drying, as long as the product can be fully dried.
- the present invention realizes the purification of the benzamide compound through the above-mentioned post treatment, and the solid material obtained by the second solid-liquid separation of this second embodiment is a sulphonic acid ion exchange resin, which can be recycled and reused.
- the present invention has no particular limitation on the methods of the first solid-liquid separation of the first embodiment, the second solid-liquid separation of the first embodiment, the first solid-liquid separation of the second embodiment, the second solid-liquid separation of the second embodiment, and the third solid- liquid separation of the second embodiment, as long as the solid-liquid separation can be realized; in the present invention, the solid-liquid separation is preferably achieved by filtration; the filtration can be performed by using a G-4 sand core funnel or a Buchner funnel, which is not particularly limited in the present invention.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010169733.3A CN111253272B (en) | 2020-03-12 | 2020-03-12 | Method for preparing benzamide compound |
PCT/EP2021/056241 WO2021180874A1 (en) | 2020-03-12 | 2021-03-11 | Method for preparing benzamide compound |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4118068A1 true EP4118068A1 (en) | 2023-01-18 |
Family
ID=70954760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP21712120.1A Pending EP4118068A1 (en) | 2020-03-12 | 2021-03-11 | Method for preparing benzamide compound |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP4118068A1 (en) |
CN (1) | CN111253272B (en) |
WO (1) | WO2021180874A1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111253272B (en) * | 2020-03-12 | 2022-11-29 | 大连凯飞化学股份有限公司 | Method for preparing benzamide compound |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01276363A (en) | 1988-04-28 | 1989-11-06 | Sharp Corp | Chiness word sentence producing device |
US5254584A (en) * | 1992-12-18 | 1993-10-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
AU725406B2 (en) * | 1996-06-28 | 2000-10-12 | It Technologies Services, S.A. | Fungicidally active N-acetonylbenzamide compounds |
AU6057998A (en) * | 1997-04-15 | 1998-10-22 | Rohm And Haas Company | Process to prepare chloroketones using oxazolines |
DE69904981T2 (en) * | 1998-04-21 | 2003-08-07 | Dow Agrosciences Llc | Metal salt catalyzed process for the production of oxazolines and subsequent production of chloroketones |
CN109810016B (en) * | 2019-02-25 | 2021-11-23 | 大连凯飞化学股份有限公司 | Enantiomer mixture and preparation method and application thereof |
CN111253272B (en) * | 2020-03-12 | 2022-11-29 | 大连凯飞化学股份有限公司 | Method for preparing benzamide compound |
-
2020
- 2020-03-12 CN CN202010169733.3A patent/CN111253272B/en active Active
-
2021
- 2021-03-11 EP EP21712120.1A patent/EP4118068A1/en active Pending
- 2021-03-11 WO PCT/EP2021/056241 patent/WO2021180874A1/en unknown
Also Published As
Publication number | Publication date |
---|---|
CN111253272B (en) | 2022-11-29 |
CN111253272A (en) | 2020-06-09 |
WO2021180874A1 (en) | 2021-09-16 |
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