CN113845487B - Preparation method of amicarbazone - Google Patents
Preparation method of amicarbazone Download PDFInfo
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- CN113845487B CN113845487B CN202111220960.5A CN202111220960A CN113845487B CN 113845487 B CN113845487 B CN 113845487B CN 202111220960 A CN202111220960 A CN 202111220960A CN 113845487 B CN113845487 B CN 113845487B
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- amicarbazone
- triazolin
- isopropyl
- amino
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- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 66
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract description 51
- YTTXGEMENREFHZ-UHFFFAOYSA-N 4-amino-3-propan-2-yl-3h-1,2,4-triazol-5-one Chemical compound CC(C)C1N=NC(=O)N1N YTTXGEMENREFHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 208000012839 conversion disease Diseases 0.000 description 13
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004321 preservation Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical compound O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 description 1
- 229960005437 etoperidone Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Abstract
The invention belongs to the field of organic synthesis, and discloses a method for synthesizing amicarbazone, which is shown in a formula (I)The structure shown. The method comprises the following steps: under the catalysis of lithium hydroxide, 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one and tert-butyl isocyanate are subjected to chemical reaction in acetonitrile medium, and the target product amicarbazone is converted with high selectivity and high yield. The method has mild reaction conditions, strong reaction operability and no strict requirement on the feeding sequence, and is particularly suitable for industrial mass production.
Description
Technical Field
The invention belongs to the technical field of organic molecular synthesis, and particularly relates to a preparation method of amicarbazone.
Background
Amicarbazone (Amicarbazone) is a triazolinone herbicide found in bayer corporation 1988, and was introduced 1999 in the briton world plant protection society in the united kingdom. Amicarbazone is a photosynthesis inhibitor, and can be absorbed by root systems and leaf surfaces to effectively prevent and treat various annual broadleaf weeds and annual gramineous weeds growing on corn fields, sugarcane fields, sweet vegetable fields, lawns and the like. The amicarbazone has the greatest advantages of safety to underground water, safety to aftercrop and long weeding time, and is considered as the best choice for replacing the environment-friendly herbicide atrazine.
Bayer company reports a synthesis method of amicarbazone in patent US5708184, which uses catalytic amount of lithium chloride and potassium hydroxide as a composite catalyst, uses methyl acetate as a reaction medium, and obtains a target product amicarbazone by reacting 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one (compound II) with tert-butyl isocyanate (compound III), wherein the reaction yield is excellent, but the product purity is lower. When only potassium hydroxide is used as a catalyst, the reaction yield is greatly reduced.
Unfortunately, the methods provided by the above patents have been tested several times, and the reaction results are not ideal, which is manifested by low reaction conversion and poor reaction selectivity. If other solvents such as acetone, tetrahydrofuran, ethylene glycol dimethyl ether, acetonitrile and the like are adopted to replace methyl acetate as a reaction medium, the reaction results are not ideal. In addition, the above reaction is usually carried out under anhydrous conditions, methyl acetate has a low boiling point and is extremely easily hydrolyzed, and it is industrially difficult to recover, thereby increasing production costs and being disadvantageous in terms of environmental protection.
In view of this, the present invention has been made.
Disclosure of Invention
The invention provides a preparation method of amicarbazone, which comprises the step of carrying out chemical reaction on 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one (compound II) and tert-butyl isocyanate (compound III) in acetonitrile under the catalysis of lithium hydroxide to obtain amicarbazone.
Preferably, the acetonitrile is used in an amount of 3-10 times, preferably 4-6 times the mass of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
Preferably, the lithium hydroxide is used in an amount of 0.01 to 0.30 times, preferably 0.02 to 0.10 times the molar equivalent of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
Preferably, the reaction temperature is 40-70 ℃.
Preferably, the reaction time is 20 to 120 minutes, preferably 30 to 60 minutes.
Preferably, the reaction is carried out in an inert atmosphere, the inert gas being nitrogen or argon.
The invention has the beneficial effects that:
the invention provides a preparation method of amicarbazone, which comprises the following steps: under the catalysis of lithium hydroxide, 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one and tert-butyl isocyanate are subjected to chemical reaction in acetonitrile medium, and the target product amicarbazone is converted with high selectivity and high yield. The method has mild reaction conditions, strong reaction operability and no strict requirement on the feeding sequence, and is particularly suitable for industrial mass production.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
The invention aims to provide a preparation method of amicarbazone (I), which comprises the steps of carrying out chemical reaction on 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one (II) and tert-butyl isocyanate (III) in acetonitrile medium under the catalysis of lithium hydroxide, and converting the 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one into amicarbazone with high selectivity and high yield, wherein the reaction equation is shown as a formula (1):
in order to achieve the above purpose, the technical scheme of the invention is as follows:
the invention provides a preparation method of amicarbazone, which comprises the step of carrying out chemical reaction on 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one (compound II) and tert-butyl isocyanate (compound III) in acetonitrile under the catalysis of lithium hydroxide to obtain a target product amicarbazone. The reaction has the characteristics of high selectivity and high yield.
The applicant found that lithium chloride in the composite catalyst reported in patent US5708184 was hardly soluble in solvents such as methyl acetate, acetone, tetrahydrofuran, ethylene glycol dimethyl ether, acetonitrile, and the like. Lithium chloride is therefore unlikely to efficiently coordinate with the reaction substrate, resulting in poor reaction selectivity. Surprisingly, it was found that when a catalytic amount of lithium hydroxide is used as a catalyst, and acetonitrile is used as a reaction medium, the chemical reaction between the compound (II) and the compound (III) proceeds smoothly, and the selectivity and conversion of the reaction are excellent, whereby amicarbazone of high quality can be produced in a high yield.
In the preparation method of the invention, acetonitrile is the optimal reaction medium. When other mediums are used, the reaction selectivity and the reaction conversion rate are obviously reduced. Further studies have found that acetonitrile is used in an amount of 3 to 10 times, preferably 4 to 6 times, the weight of compound (II). If the dosage of acetonitrile is too small, the reactant cannot be fully dissolved, and the reaction conversion rate and the product yield are reduced; if the acetonitrile dosage is too large, the concentration of the reactant in the medium is too low, the reaction rate is reduced, and the production efficiency is reduced.
In the preparation method of the invention, the catalyst is different from the composite catalyst (lithium chloride and potassium hydroxide) in the patent US5708184, and lithium hydroxide is used as the catalyst. The catalyst is used in an amount of 0.01 to 0.30 times, preferably 0.02 to 0.10 times the molar equivalent of the compound (II).
In the preparation method of the invention, the adopted reaction conditions are mild, and no obvious heat is released. The preferred reaction temperature is 40-70℃at which the reaction proceeds smoothly.
In the preparation method of the invention, the reaction time is 20-120 minutes, preferably 30-60 minutes.
In the preparation method of the invention, the reaction is carried out in an inert atmosphere, and the inert gas is nitrogen or argon.
The preparation method of the invention has strong operability and no strict requirement on the feeding sequence, and can adopt a method of dripping tert-butyl isocyanate into the reaction mixture or adopt a one-time feeding mode for operation. After the reaction is finished, the solvent is recovered through negative pressure concentration, and the recovered solvent can be directly used.
The raw material compound (II) for experiments is synthesized in a laboratory and has the purity of 99.0 percent; compound (III) was provided by Jiangsu glong chemical company, limited, with a purity of 99.5%. The purity of each material was obtained by Gas Chromatography (GC) analysis.
Example 1
360.00g of acetonitrile, 57.29g (0.575 mol) of tert-butyl isocyanate, 0.71g (0.030 mol) of powdery lithium hydroxide and 71.80g (0.500 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one were successively introduced into a reaction flask under the protection of a nitrogen stream. Stirring is started, the temperature is raised to 60 ℃, and the reaction is completed after 60 minutes of heat preservation. 6.00g of acetic acid was added to neutralize the alkali in the reaction system, and the reaction was sampled and analyzed by High Performance Liquid Chromatography (HPLC), the reaction conversion was 97.9%, and the reaction selectivity was 98.2%.
After concentrating under negative pressure and desolventizing, 175ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 116.19g amicarbazone as a white powdery solid with a purity of 97.6% and a yield of 94.0%.
Example 2
360.00g of acetonitrile, 0.71g (0.030 mol) of powdery lithium hydroxide and 71.80g (0.500 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one were successively introduced into a reaction flask under the protection of a nitrogen stream. Stirring was started, the temperature was raised to 60℃and 57.29g (0.575 mol) of t-butyl isocyanate was added dropwise to the reaction solution over 30 minutes, followed by heat preservation for 60 minutes. After the completion of the reaction, 6.00g of acetic acid was added to neutralize the alkali in the reaction system, and the reaction was sampled and analyzed by HPLC, with a reaction conversion of 97.8% and a reaction selectivity of 98.7%.
After concentrating under negative pressure and desolventizing, 175ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 116.78g amicarbazone as a white powdery solid with a purity of 97.7% and a yield of 94.6%.
The reactants and amounts of the reactants in examples 1 and 2 were the same except that the reaction was carried out by directly mixing the reactants in example 1, and the reaction was carried out by dropwise adding tert-butyl isocyanate after mixing acetonitrile, lithium hydroxide and 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one in example 2. The reaction products of the two have higher purity and yield.
Comparative example 1
360.00g of methyl acetate, 57.29g (0.575 mol) of tert-butyl isocyanate, 0.71g (0.030 mol) of powdered lithium hydroxide and 71.80g (0.500 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one are introduced into a reaction flask in this order under the protection of a nitrogen stream. Stirring was started, the temperature was raised to reflux (about 60 ℃ C.) and the temperature was maintained for 60 minutes. After the completion of the reaction, 6.00g of acetic acid was added to neutralize the alkali in the reaction system, and the reaction was sampled and analyzed by HPLC, with a reaction conversion of 91.2% and a reaction selectivity of 92.8%.
After concentrating under negative pressure and desolventizing, 175ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 83.86g amicarbazone as a white powdery solid with a purity of 93.8% and a yield of 65.2%.
In comparative example 1, in which the medium was replaced with methyl acetate by acetonitrile, the reaction conversion, reaction selectivity and product purity were all reduced to different extents, and the reduction in product yield was most remarkable.
Comparative example 2
360.00g of methyl acetate, 0.71g (0.030 mol) of powdered lithium hydroxide and 71.80g (0.500 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one were introduced into a reaction flask in this order under the protection of a nitrogen stream. Stirring was started, the temperature was raised to reflux (about 60 ℃ C.), 57.29g (0.575 mol) of t-butyl isocyanate was added dropwise to the reaction solution over 30 minutes, followed by heat preservation for 60 minutes. After the completion of the reaction, 6.00g of acetic acid was added to neutralize the alkali in the reaction system, and the reaction was sampled and analyzed by HPLC, with a reaction conversion of 88.7% and a reaction selectivity of 95.3%.
After concentrating under negative pressure and desolventizing, 175ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 83.50g amicarbazone as a white powdery solid with a purity of 94.2% and a yield of 65.2%.
In comparative example 2, in which the medium was replaced with methyl acetate by acetonitrile, the reaction conversion, reaction selectivity and product purity were all reduced to different extents, and the reduction in product yield was most remarkable.
Comparative example 3
72.00g of acetonitrile, 0.96g (0.015 mol) of potassium hydroxide, 0.72g (0.017 mol) of powdery lithium chloride and 14.36g (0.100 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one were successively introduced into a reaction flask under the protection of a nitrogen stream. Stirring was started, the temperature was raised to 60℃and 11.46g (0.115 mol) of t-butyl isocyanate was added dropwise to the reaction solution over 30 minutes, followed by heat preservation for 60 minutes. After completion of the reaction, 1.20g of acetic acid was added, and the sample was taken for HPLC analysis, and the reaction conversion was 85.5% and the reaction selectivity was 81.3%.
After concentrating under negative pressure and desolventizing, 35ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 16.74g amicarbazone as a white solid with a purity of 93.1% and a yield of 64.6%.
In comparative example 3, in which the catalyst was replaced by a single lithium hydroxide catalyst as compared with example 2, the reaction conversion, reaction selectivity and product purity were all reduced to different extents, and the reduction in product yield was most remarkable.
Comparative example 4
72.00g of methyl acetate, 0.96g (0.015 mol) of potassium hydroxide, 0.72g (0.017 mol) of powdery lithium chloride and 14.36g (0.100 mol) of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one were successively introduced into a reaction flask under the protection of a nitrogen stream. Stirring was started, the temperature was raised to reflux (about 60 ℃ C.), and 11.46g (0.115 mol) of t-butyl isocyanate was added dropwise to the reaction solution over 30 minutes, followed by heat preservation for 60 minutes. After completion of the reaction, 1.20g of acetic acid was added, and the sample was taken for HPLC analysis, and the reaction conversion was 78.8% and the reaction selectivity was 79.6%.
After concentrating under negative pressure and desolventizing, 35ml of water is added, stirred, cooled to 10 ℃ and filtered. The filter cake was dried to give 16.04g amicarbazone as a white solid with a purity of 85.3% and a yield of 56.7%.
Comparative example 4 was a further decrease in the reaction result, which was shown to be low in reaction conversion and poor in reaction selectivity, by changing both the medium and the catalyst as compared with comparative example 3.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (9)
1. The preparation method of amicarbazone is characterized in that under the catalysis of lithium hydroxide, 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one and tert-butyl isocyanate are subjected to chemical reaction in acetonitrile to obtain amicarbazone;
the dosage of the acetonitrile is 3-10 times of the mass of the 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
2. The method according to claim 1, wherein the acetonitrile is used in an amount of 4 to 6 times by mass of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
3. The method according to claim 1, wherein the lithium hydroxide is used in an amount of 0.01 to 0.30 times the molar equivalent of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
4. A method according to claim 3, wherein the lithium hydroxide is used in an amount of 0.02 to 0.10 times the molar equivalent of 3-isopropyl-4-amino-1, 2, 4-triazolin-5-one.
5. The method of claim 1, wherein the reaction temperature of the chemical reaction is 40-70 ℃.
6. The method of claim 1, wherein the reaction time is 20-120 minutes.
7. The method of claim 6, wherein the reaction time is 30-60 minutes.
8. The method of claim 1, wherein the reaction is carried out in an inert atmosphere.
9. The method of claim 8, wherein the inert atmosphere is nitrogen or argon.
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| CN104968649A (en) * | 2013-01-25 | 2015-10-07 | Ks试验研究株式会社 | Method for preparing amicarbazone |
| CN108699010A (en) * | 2016-03-10 | 2018-10-23 | 江苏龙灯化学有限公司 | The new model of amicarbazone, Its Preparation Method And Use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104968649A (en) * | 2013-01-25 | 2015-10-07 | Ks试验研究株式会社 | Method for preparing amicarbazone |
| CN108699010A (en) * | 2016-03-10 | 2018-10-23 | 江苏龙灯化学有限公司 | The new model of amicarbazone, Its Preparation Method And Use |
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