CN110028450A - A kind of preparation method of pyrazol acid amide compounds - Google Patents
A kind of preparation method of pyrazol acid amide compounds Download PDFInfo
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- CN110028450A CN110028450A CN201810031198.8A CN201810031198A CN110028450A CN 110028450 A CN110028450 A CN 110028450A CN 201810031198 A CN201810031198 A CN 201810031198A CN 110028450 A CN110028450 A CN 110028450A
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- -1 pyrazol acid amide compounds Chemical class 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006482 condensation reaction Methods 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 7
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 58
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- JQDCYDWZWBUECX-UHFFFAOYSA-N 3-(difluoromethyl)-1-methylpyrazole Chemical compound CN1C=CC(C(F)F)=N1 JQDCYDWZWBUECX-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000011230 binding agent Substances 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 239000000417 fungicide Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 30
- 239000012065 filter cake Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GYUFLTOWUVCCNO-UHFFFAOYSA-N 1-(difluoromethyl)pyrazole Chemical compound FC(F)N1C=CC=N1 GYUFLTOWUVCCNO-UHFFFAOYSA-N 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- QASKCGNZJHBTDJ-UHFFFAOYSA-N [SiH4].BrCCCCC Chemical compound [SiH4].BrCCCCC QASKCGNZJHBTDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Abstract
The invention belongs to organic synthesis fields, and in particular to a kind of preparation method of pyrazol acid amide fungicide.Reaction is that substituted aniline shown in carboxylic acid halides shown in general formula II and general formula III carries out condensation reaction in solvent under 70 DEG C to solvent reflux temperature, vacuum condition, obtains pyrazol acid amide compounds shown in general formula I, reaction equation is as follows, and each group is shown in specification in formula.It selects 1- methyl -3- difluoromethyl pyrazole -4- formyl halide and substituted aniline to exist in no acid binding agent in preparation process of the present invention, react the 3- difluoromethyl pyrazole amides compound of acquisition high yield under reduced pressure, and the use without acid binding agent in entire reaction process, the generation for both reducing the three wastes in reaction also increase the safety of reaction.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of preparation method of pyrazol acid amide fungicide.
Background technique
Pyrazol acid amide compounds have certain bactericidal activity, disclose the chemical combination as shown in general formula I in CN104649973A
Object has good bactericidal activity to rice sheath blight disease.
The preparation method of two kinds of pyrazol acid amide compounds is also disclosed in CN104649973A: by 3- difluoromethyl pyrrole
Azoles acyl chloride compound is reacted to obtain target product with substituted aniline under alkaline condition；By amidophenol class compound and
Bromo pentane silane reacts under alkaline condition obtains target product.But that there are reaction raw materials is many kinds of for the two methods, after reaction
The three wastes are more and processing is difficult, and the very low critical process problem of yield.
All the time, technical staff is dedicated to constantly researching and developing new, more advanced reasonable, more environmentally-friendly preparation side
Method, to obtain, quality is more excellent, price is lower efficiently, the fungicide of safety.
Summary of the invention
The purpose of the present invention is to provide a kind of sides for preparing pyrazol acid amide compounds more easyly, more environmentally-friendly
Method.
To achieve the above object, the invention adopts a technical scheme as:
A kind of preparation method of pyrazol acid amide compounds, reaction equation are as follows:
In formula:
R1Selected from hydrogen or methyl；
R2Selected from methyl, ethyl, propyl or isopropyl；
X is selected from Cl or Br；
Reaction are as follows: substituted aniline shown in carboxylic acid halides shown in general formula II and general formula III is in solvent at 70 DEG C to solvent refluxing
Condensation reaction under temperature, vacuum condition obtains pyrazol acid amide compounds shown in general formula I.
The condensation reaction time is 0.5-8 hours；Carboxylic acid halides shown in the general formula II rubs with substituted aniline shown in general formula III
You are than being 0.8-1.5:1.
The condensation reaction is under -0.1MPa~-0.01MPa pressure, and the reaction time is 1-6 hours, the general formula II institute
Show that substituted aniline molar ratio shown in carboxylic acid halides and general formula III is 0.9-1.2:1.
Under -0.05MPa~-0.01MPa pressure, the reaction time is 3-5 hours for the condensation reaction.
The solvent is selected from methylene chloride, dichloroethanes, chloroform, carbon tetrachloride, pentane, hexane, octane, benzene, toluene, two
Toluene, methyl acetate, ethyl acetate, propyl acetate, acetonitrile, butyronitrile, ether, tetrahydrofuran, dioxane, acetone, butanone, first
Base propyl ketone, methyl isopropyl Ketone, methyl butyl ketone, methyl iso-butyl ketone (MIBK), ethyl isobutylo ketone.
The solvent is selected from toluene or acetonitrile.
Advantage for present invention:
1- methyl -3- difluoromethyl pyrazole -4- formyl halide and substituted aniline is selected to tie up acid in nothing in preparation process of the present invention
Reaction obtains the 3- difluoromethyl pyrazole amides compound of high yield, and entire reaction process under agent presence, reduced pressure
The use of middle no acid binding agent, the generation for both reducing the three wastes in reaction also increase the safety of reaction.
Specific embodiment
Following synthesis example can be used to further illustrate the present invention, but be not intended to limit the present invention.
Embodiment 1
The synthesis of compound 1
The toluene solution of-the 3- of methyl containing 2- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, so
The toluene solution of-the 3- of methyl containing 1- difluoromethyl pyrazole -4- formyl chloride (21.4 grams, 0.11 mole), room is added dropwise at room temperature afterwards
This reaction solution after ten minutes, is evacuated to -0.02MPa and is slowly heated to flow back by temperature stirring, and reflux has been reacted after 5 hours
Finish, reaction solution is directly cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of toluene, finally obtains 32.4 grams admittedly
Body, content 98.1%, yield 90.5%.
Embodiment 2
The toluene solution of 2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, then
The toluene solution of 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride (21.4 grams, 0.11 mole) is added dropwise at room temperature, room temperature is stirred
It mixes after ten minutes, this reaction solution is evacuated to -0.05MPa and is slowly heated to flow back, end of reaction after reflux 5 hours, instead
Liquid is answered directly to be cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of toluene, finally obtains 32 grams of solids, content
97.5%, yield 88.8%.
Embodiment 3
The toluene solution of 2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, then
The toluene solution of 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride (19.46 grams, 0.1 mole) is added dropwise at room temperature, room temperature is stirred
It mixes after ten minutes, this reaction solution is evacuated to -0.02MPa and is slowly heated to flow back, end of reaction after reflux 5 hours, instead
Liquid is answered directly to be cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of toluene, finally obtains 31 grams of solids, content
98.5%, yield 86.9%.
Embodiment 4
The acetonitrile solution of 2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, then
The acetonitrile solution of 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride (19.46 grams, 0.1 mole) is added dropwise at room temperature, room temperature is stirred
It mixes after ten minutes, this reaction solution is evacuated to -0.02MPa and is warming up to reflux, end of reaction after 5 hours, reaction solution is direct
It is cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of acetonitriles, finally obtain 29.4 grams of solids, content 96.3%,
Yield 80.6%.
Embodiment 5
The toluene solution of 2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, then
The toluene solution of 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride (19.46 grams, 0.1 mole) is added dropwise at room temperature, room temperature is stirred
It mixes after ten minutes, this reaction solution is evacuated to -0.02MPa and is warming up to 70 DEG C of reactions, end of reaction after 5 hours, reaction solution
Directly it is cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of toluene, finally obtains 30.2 grams of solids, content
96.6%, yield 83%.
Embodiment 6
The toluene solution of 2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole) is added in reaction flask, then
The toluene solution of 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride (19.46 grams, 0.1 mole) is added dropwise at room temperature, room temperature is stirred
It mixes after ten minutes, this reaction solution is evacuated to -0.05MPa and is warming up to 70 DEG C of reactions, end of reaction after 5 hours, reaction solution
Directly it is cooled to room temperature.Reaction solution is filtered, filter cake is eluted with 30 grams of toluene, finally obtains 29.6 grams of solids, content
96.8%, yield 81.5%.
Comparative examples
Compound 1 is synthesized according to the method that CN104649973A is provided.
2- methyl -3- (2- amoxy) aniline (19.33 grams, 0.1 mole), triethylamine (10.12 are added in reaction flask
Gram, 0.1 mole) and 100 milliliters of methylene chloride, lower dropwise addition 1- methyl -3- difluoromethyl pyrazole -4- formyl chloride is stirred at room temperature
100 milliliters of dichloromethane solution of (19.46 grams, 0.1 mole).Drop finishes, and reacts at room temperature, end of reaction after 3 hours.Reaction solution
It is poured into 30 milliliters of water, takes organic layer, organic layer uses saturated sodium bicarbonate aqueous solution, saturated common salt water washing, anhydrous sulphur respectively
Sour magnesium is dry, and solvent to the greatest extent is steamed in decompression.Residue is obtained by column chromatography purification (leacheate: ethyl acetate: petroleum ether=1:2)
23.67 g of compound 1, yield 67.4%.
Claims (6)
1. a kind of preparation method of pyrazol acid amide compounds, it is characterised in that: reaction equation is as follows:
In formula:
R1Selected from hydrogen or methyl；
R2Selected from methyl, ethyl, propyl or isopropyl；
X is selected from Cl or Br；
Reaction are as follows: substituted aniline shown in carboxylic acid halides shown in general formula II and general formula III in solvent 70 DEG C to solvent reflux temperature,
Condensation reaction is carried out under vacuum condition, obtains pyrazol acid amide compounds shown in general formula I.
2. preparation method described in accordance with the claim 1, it is characterised in that: the condensation reaction time is 0.5-8 hours；It is described
Substituted aniline molar ratio shown in carboxylic acid halides shown in general formula II and general formula III is 0.8-1.5:1.
3. preparation method according to claim 1 or 2, it is characterised in that: the condensation reaction -0.1MPa~-
Under 0.01MPa pressure, the reaction time is 1-6 hours, substituted aniline molar ratio shown in carboxylic acid halides shown in the general formula II and general formula III
For 0.9-1.2:1.
4. preparation method described in accordance with the claim 3, it is characterised in that: the condensation reaction is in -0.05MPa~-0.01MPa
Under pressure, the reaction time is 3-5 hours.
5. preparation method described in accordance with the claim 1, it is characterised in that: the solvent is selected from methylene chloride, dichloroethanes, chlorine
Imitative, carbon tetrachloride, pentane, hexane, octane, benzene,toluene,xylene, methyl acetate, ethyl acetate, propyl acetate, acetonitrile, fourth
Nitrile, ether, tetrahydrofuran, dioxane, acetone, butanone, methyl propyl ketone, methyl isopropyl Ketone, methyl butyl ketone, methyl are different
Butyl ketone, ethyl isobutylo ketone.
6. preparation method according to claim 5, it is characterised in that: the solvent is selected from toluene or acetonitrile.
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| CN201810031198.8A CN110028450A (en) | 2018-01-12 | 2018-01-12 | A kind of preparation method of pyrazol acid amide compounds |
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| CN201810031198.8A CN110028450A (en) | 2018-01-12 | 2018-01-12 | A kind of preparation method of pyrazol acid amide compounds |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021031984A1 (en) * | 2019-08-16 | 2021-02-25 | 沈阳中化农药化工研发有限公司 | Carboxylic acid oxime ester compound and use thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1816529A (en) * | 2003-05-01 | 2006-08-09 | 布里斯托尔-迈尔斯.斯奎布公司 | Pyrazole-amide compounds useful as kinase inhibitors |
| WO2010075197A1 (en) * | 2008-12-23 | 2010-07-01 | Allergan, Inc. | Kinase inhibitors |
| CN102015649A (en) * | 2008-05-08 | 2011-04-13 | 巴斯夫欧洲公司 | Method for manufacturing aryl carboxamides |
| CN104649973A (en) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | Pyrazole amide compound and application thereof |
-
2018
- 2018-01-12 CN CN201810031198.8A patent/CN110028450A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1816529A (en) * | 2003-05-01 | 2006-08-09 | 布里斯托尔-迈尔斯.斯奎布公司 | Pyrazole-amide compounds useful as kinase inhibitors |
| CN102015649A (en) * | 2008-05-08 | 2011-04-13 | 巴斯夫欧洲公司 | Method for manufacturing aryl carboxamides |
| WO2010075197A1 (en) * | 2008-12-23 | 2010-07-01 | Allergan, Inc. | Kinase inhibitors |
| CN104649973A (en) * | 2013-11-25 | 2015-05-27 | 中国中化股份有限公司 | Pyrazole amide compound and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 姬文娟等: ""1-（3-氯吡啶-2-基）-5-二氟甲基-1H-4-吡唑酰胺类化合物的合成及杀菌活性"", 《农药学学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021031984A1 (en) * | 2019-08-16 | 2021-02-25 | 沈阳中化农药化工研发有限公司 | Carboxylic acid oxime ester compound and use thereof |
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Application publication date: 20190719 |