CN116715626A - Intermediate for preparing imidazolinone compound (I) and application thereof - Google Patents
Intermediate for preparing imidazolinone compound (I) and application thereof Download PDFInfo
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- CN116715626A CN116715626A CN202310654121.7A CN202310654121A CN116715626A CN 116715626 A CN116715626 A CN 116715626A CN 202310654121 A CN202310654121 A CN 202310654121A CN 116715626 A CN116715626 A CN 116715626A
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- Prior art keywords
- alkyl
- general formula
- compound
- solvent
- imidazolinone
- Prior art date
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- -1 imidazolinone compound Chemical class 0.000 title claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000001412 amines Chemical class 0.000 claims abstract description 26
- 239000003513 alkali Substances 0.000 claims abstract description 20
- 238000009835 boiling Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 20
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 20
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 18
- WYROLENTHWJFLR-ACLDMZEESA-N queuine Chemical compound C1=2C(=O)NC(N)=NC=2NC=C1CN[C@H]1C=C[C@H](O)[C@@H]1O WYROLENTHWJFLR-ACLDMZEESA-N 0.000 claims description 17
- YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical compound CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005059 halophenyl group Chemical group 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 4
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 229940117389 dichlorobenzene Drugs 0.000 claims description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 8
- 239000001301 oxygen Substances 0.000 abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 abstract description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HNNJFUDLLWOVKZ-UHFFFAOYSA-N 2-aminobutanamide Chemical compound CCC(N)C(N)=O HNNJFUDLLWOVKZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- KECAIOAFWPFNPY-UHFFFAOYSA-N CCOC(=O)C1=C(C=C(C=N1)CBr)C(=O)O Chemical compound CCOC(=O)C1=C(C=C(C=N1)CBr)C(=O)O KECAIOAFWPFNPY-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000006450 cyclopropyl cyclopropyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000006198 methoxylation reaction Methods 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to compound synthesis, in particular to an intermediate for preparing an imidazolinone compound (I) and application thereof. An intermediate for preparing imidazolone compound (I) with the structural formula as follows
Description
Technical Field
The invention relates to compound synthesis, in particular to an intermediate for preparing an imidazolinone compound (I) and application thereof.
Background
The imidazolinone compound is developed by American cyanamide company, has high herbicidal activity and has the characteristics of high efficiency, broad spectrum and low toxicity. Imidazolone compounds are disclosed in patents US4798619 and US5334576 as highly potent, broad spectrum, environmentally friendly herbicides. The imidazolinone compound (I) is a soybean field herbicide developed by American cyanamide company, is used as an ALS inhibitor to inhibit the biosynthesis of side chain amino acids, has high activity, low dosage and broad herbicide spectrum, and has high use value, and can be used for pre-emergence and post-emergence application.
Various synthetic methods for these compounds are known from the literature, see for example EP0322616, EP0747360, EP0933362 or Q.Bi et al, modern Agrochemical6 (2) (2007) 10-14. Although industrial scale synthesis is carried out by these methods, there is still room for improvement, especially in economic and ecological aspects, such as overall yield improvement or avoidance of specific solvents or reagents.
The American cyanamide company in patent US5288866 discloses a process for the preparation of 5, 6-disubstituted-3-pyridylmethylammonium halides by halogenation of the corresponding 5, 6-disubstituted-3-methyl-pyridines followed by reaction with trialkylamines or cyclic unsaturated or saturated amines. The trialkylamine has large smell, is easy to volatilize, and has great harm to human bodies and environment in the production process.
The preparation method of the compound is disclosed in patent US5973154 by the American cyanamide company and patent WO2010054954 by the Pasteur company, and the ammonium salt intermediate prepared in the patent is subjected to etherification reaction with sodium methoxide and then reacts with aminobutanamide to prepare the compound, or the imidazolinone compound (I) is prepared by a method of hydrolyzing to diacid and then converting to anhydride, so that the problems of more reaction steps and large wastewater amount exist.
The preparation method of the compound is also disclosed in the patent WO2018091964 of Andao wheat company, and the key process problems of more reaction steps, low reaction yield and the like still exist.
Although industrial production of imidazolinones has been carried out, there is room for improvement from the standpoint of process, especially from the standpoint of both economy and environmental protection, such as simplification of the reaction process, improvement of the reaction yield, and avoidance of the use of special solvents, etc.
In the past, technicians have been devoted to continuously researching and developing new, more advanced, reasonable and more environment-friendly preparation methods in order to obtain efficient and safe herbicides with better quality and lower price.
Disclosure of Invention
The invention aims to provide an intermediate for preparing an imidazolinone compound (I) with simplicity, environmental protection and low cost and application thereof.
In order to achieve the above purpose, the invention adopts the technical scheme that:
an intermediate for preparing imidazolone compound (I) with the structural formula as follows
In the method, in the process of the invention,
R 1 、R 2 independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, phenyl, halophenyl, phenyl C 1 -C 6 Alkyl or halophenyl C 1 -C 6 An alkyl group;
x is selected from chlorine or bromine;
Q + selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 3 -C 6 Cycloalkyl C 1 -C 6 Alkyl, C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, C 1 -C 6 Alkyldi (oxy C) 1 -C 6 Alkyl group, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl NR 3 R 4 。
Preferably, in the intermediate form,
R 1 、R 2 independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl;
x is selected from bromine;
Q + selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 An alkyl group.
Use of said intermediate for the preparation of an imidazolinone compound (I), said intermediate compound being useful in the preparation of an imidazolinone compound.
A process for preparing an imidazolinone compound (I) by reacting
In the general formula II
R 1 、R 2 Independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, phenyl, halophenyl, phenyl C 1 -C 6 Alkyl or halophenyl C 1 -C 6 An alkyl group;
wherein X is selected from chlorine or bromine;
q in + Selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 3 -C 6 Cycloalkyl C 1 -C 6 Alkyl, C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, C 1 -C 6 Alkyldi (oxy C) 1 -C 6 Alkyl group, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl NR 3 R 4 。
Specifically, a compound of a general formula III is added into a solvent A, an alcohol solution of an amine base Q is dropwise added in the boiling point range of the solvent A at 0 ℃ to obtain a quaternary ammonium salt compound of the general formula II after reaction; the quaternary ammonium salt compound of the general formula II reacts with 2-amino-2, 3-dimethylbutyramide in a solvent B at a temperature ranging from 0 ℃ to the boiling point of the solvent B in the presence of alkali, and the imidazolinone compound (I) is obtained by acidification after the reaction. Wherein the mass ratio of the amine base Q to the alcohol in the alcohol solution of the amine base Q is 1:0.5-3.5, and the selection of the Q in the amine base Q is consistent with the description in the general formula.
The alcohol is selected from methanol, ethanol, isopropanol and tert-butanol; the solvent A is selected from one or more of dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene or dichlorobenzene;
the alkali is selected from sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide or potassium tert-butoxide; the acid is one or more of hydrochloric acid, sulfuric acid and acetic acid; the solvent B is one or more selected from methanol, ethanol, isopropanol, tertiary butanol, dichloromethane, carbon tetrachloride, dichloroethane, toluene, chlorobenzene or dichlorobenzene.
The compound shown in the general formula III is added into excessive solvent A at the temperature of between 0 ℃ and the boiling point range of the solvent A, then an alcohol solution of amine base Q is added dropwise, salification reaction is carried out for 0.5 to 10 hours, and the compound shown in the general formula II is obtained by filtration; wherein the molar ratio of the compound shown in the general formula III to the amine base Q is 1:1-1.5.
The compound shown in the general formula III is added into excessive solvent A at the temperature of 20 ℃ to the boiling point range of the solvent A, then an alcohol solution of amine base Q is added dropwise, salification reaction is carried out for 0.5-6 hours, and the compound shown in the general formula II is obtained by filtration; wherein the molar ratio of the compound shown in the general formula III to the amine base Q is 1:1-1.3;
the alcohol is selected from methanol, ethanol and isopropanol; the solvent A is selected from carbon tetrachloride, chloroform, dichloroethane and chlorobenzene.
The quaternary ammonium salt compound shown in the general formula II and 2-amino-2, 3-dimethylbutyramide are subjected to condensation reaction in an excessive solvent B in the presence of alkali at the temperature of 0 ℃ to the boiling point range of the solvent B for 0.5-10 hours, and then acidized to obtain an imidazolinone compound (I); wherein,,
the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the 2-amino-2, 3-dimethylbutyramide is 1:1-1.5; the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the alkali is 1:2-5.
The quaternary ammonium salt compound shown in the general formula II and 2-amino-2, 3-dimethylbutyramide are subjected to condensation reaction in an excessive solvent B in the presence of alkali at the temperature of 20 ℃ to the boiling point range of the solvent B for 0.5-8 hours, and then acidized to obtain an imidazolinone compound (I); wherein the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the 2-amino-2, 3-dimethylbutyramide is 1:1-1.2; the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the alkali is 1:3-4; the solvent B is selected from dichloroethane, toluene or chlorobenzene, and the base is selected from sodium methoxide, potassium methoxide or sodium ethoxide; the acid is selected from hydrochloric acid or sulfuric acid.
In the definition of compounds of the general formula II given above, the terms used in the collection are defined as follows:
alkyl refers to straight or branched chain forms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and the like. Cycloalkyl is meant to include groups in the form of cyclic chains such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Alkenyl refers to straight or branched alkenyl groups such as vinyl, 1-propenyl, 2-propenyl, butenyl, pentenyl, hexenyl and the like. Alkynyl refers to straight or branched chain alkynyl groups such as 1-propynyl, 2-propynyl, butynyl, pentynyl, hexynyl and the like. Alkoxy refers to a group having an oxygen atom attached to the end of the alkyl group, such as methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, and the like. A5-7 membered heterocyclic ring containing 1-4 hetero atoms means a 5-7 membered heterocyclic ring containing 1-4 hetero atoms without aromatic character, such as tetrahydrofuran, imidazolinone, caprolactam, etc.
Compared with the prior art, the invention has the following characteristics:
the compound of the general formula II is synthesized by reacting the compound of the general formula III with oxygen-containing amine alkali, wherein the oxygen-containing amine alkali forms more hydrogen bonds among molecules of the oxygen-containing amine alkali compared with trimethylamine, triethylamine and the like in the traditional production process, so that the boiling point of the oxygen-containing amine alkali is higher, the volatilization is more difficult, the generation of strong fishy smell in the production process is avoided, the environmental pollution is reduced, and the health risk of workers is reduced.
Compared with the conventional alkyl quaternary ammonium salt, the compound shown in the general formula II is easier to dissociate during the next reaction, and further easier to react.
The present invention prepares the imidazolinone compound (I) by a one-step process of methoxylation and cyclization of the compound of formula II. The synthesis process of the compound (I) avoids the generation of odor, simplifies the operation process, has mild reaction conditions, reduces the amount of three wastes and has high product content.
Detailed Description
The following description of the embodiments of the invention will be presented in conjunction with the examples, it being noted that what is described herein
The specific embodiments are described for the purpose of illustrating and explaining the present invention, and are not limited to the present invention.
Example 1
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) and dichloroethane are heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) and methanol are added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 37.1g of product with 97.2 percent of content and 95.6 percent of yield are obtained. LC-MS [ M ]] + ＝297.19。
Example 2
The temperature of the ethyl 5-bromomethylpyridine-2, 3-diformate (31.61 g,0.1 mol) dichloroethane solution is raised to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) methanol solution is added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 38.9g of the product with the content of 95.0 percent and the yield of 91.2 percent is obtained. LC-MS [ M ]] + ＝325.21。
Example 3
5-Bromomethylpyridine-2, 3-dicarboxylic acid methyl esterThe temperature of the dichloroethane solution of the ester (28.81 g,0.1 mol) was raised to 50 ℃, the methanol solution of triethanolamine (16.41 g,0.11 mol) was added dropwise to the reaction system, the temperature was kept for 6 hours after the completion of the dropwise addition, and the product was obtained by cooling and post-treatment, and the yield was 92.5%. LC-MS [ M ]] + ＝357.19。
Example 4
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) containing chlorobenzene solution is heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) methanol solution is added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 36.1g of product with 97.6 percent of content and 93.4 percent of yield are obtained.
Example 5
Methyl 5-bromopyridine-2, 3-dicarboxylic acid (28.81 g,0.1 mol) carbon tetrachloride solution is heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) methanol solution is dropwise added into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 36.8g of a product with the content of 97.5% and the yield of 95.1% is obtained.
Example 6
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) chloroform solution is heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) methanol solution is added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 35.9g of product with the content of 98.1% and the yield of 93.3% is obtained.
Example 7
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) and dichloroethane are heated to 45 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) and methanol are added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 35.5g of product with 97.3 percent of content and 91.6 percent of yield are obtained.
Example 8
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) and dichloroethane are heated to 60 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) and methanol are added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 35.3g of product with 98.1 percent of content and 91.8 percent of yield are obtained.
Example 9
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) and dichloroethane are heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) and methanol are added dropwise into the reaction system, the temperature is kept for 2 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 34.5g of the product with 96.2 percent of content and 88.0 percent of yield is obtained.
Example 10
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) and dichloroethane are heated to 50 ℃, N-dimethylethanolamine (9.81 g,0.11 mol) and methanol are added dropwise into the reaction system, the temperature is kept for 5 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 36.9g of the product with 97.8 percent of content and 95.7 percent of yield are obtained.
Example 11
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) dichloroethane solution is heated to 50 ℃, N-dimethylethanolamine (11.59 g,0.13 mol) methanol solution is added dropwise into the reaction system, the temperature is kept for 5 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 36.7g of product with 96.9 percent of content and 94.3 percent of yield is obtained.
Example 12
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) dichloroethane solution is heated to 50 ℃, N-dimethylethanolamine (11.59 g,0.13 mol) methanol solution is added dropwise into the reaction system, the temperature is kept for 5 hours after the dropwise addition, the temperature is reduced, the post-treatment is carried out, and 36.9g of product with 97.1 percent of content and 95.0 percent of yield are obtained.
Other compounds of formula II, the partial compounds of which are shown in Table 1, can be obtained by replacing the amine base Q in the starting materials according to the method described above.
TABLE 1
Example 13
To the reaction flask was added N- (5, 6-dimethoxycarbonylpyridine-3-methyl) -N- (2-hydroxyethyl) -N, N-dimethylammonium bromide (37.73 g,0.10 mol), 30% sodium methoxide solution (63.03 g,0.35 mol) prepared in example 1, and 150mL of toluene as a solvent at room temperature. Dropwise adding toluene solution of 2-amino-2, 3-dimethylbutyramide (16.93 g,0.13 mol) under stirring, heating to 60deg.C after the dropwise addition, and keepingReacting for 2 hours at a temperature; after the reaction, the mixture was cooled to room temperature, diluted with water and separated to obtain a water phase. The aqueous phase was acidified with hydrochloric acid at ph=3, and filtered and dried to give 26.3g of an imidazolinone compound (I) as a white solid, the content of which was 98.1%, and the yield was 84.5%. LC-MS [ M+H ]] + ＝306.22、[M+Na] + ＝328.12。
Example 14
To the reaction flask was added N- (5, 6-diethoxycarbonyl pyridine-3-methyl) -N- (2-hydroxyethyl) -N, N-dimethylammonium bromide (40.53 g,0.10 mol), 30% sodium methoxide solution (63.03 g,0.35 mol) prepared in example 1, and 150mL of toluene as a solvent at room temperature. Dropwise adding a toluene solution of 2-amino-2, 3-dimethylbutyramide (16.93 g,0.13 mol) under stirring, heating to 60 ℃ after the dropwise adding, and preserving heat for 2 hours; after the reaction, the mixture was cooled to room temperature, diluted with water and separated to obtain a water phase. The aqueous phase was acidified with hydrochloric acid at ph=3, and filtered and dried to give 25.8g of an imidazolinone compound (I) as a white solid, the content of which was 98.3%, and the yield was 83.1%. LC-MS [ M+H ]] + ＝306.23、[M+Na] + ＝328.15。
Example 15
N- (5, 6-Dimethoxycarbonylpyridine-3-methyl) -2-hydroxy-N, N-di (2-ethoxy) ethyl ammonium bromide (43.73 g,0.10 mol), 30% sodium methoxide solution (63.03 g,0.35 mol) prepared in example 3 and 150mL of toluene as a solvent were added to the reaction flask at room temperature. Dropwise adding a toluene solution of 2-amino-2, 3-dimethylbutyramide (16.93 g,0.13 mol) under stirring, heating to 60 ℃ after the dropwise adding, and preserving heat for 2 hours; after the reaction, the mixture was cooled to room temperature, diluted with water and separated to obtain a water phase. The aqueous phase was acidified with hydrochloric acid at ph=3, and filtered and dried to give 26.3g of an imidazolinone compound (I) as a white solid, the content of which was 97.6%, and the yield was 84.1%.
Example 16
To a reaction flask was added N- (5, 6-dimethoxycarbonylpyridine-3-methyl) -N- (2-hydroxyethyl) -N, N-dimethylammonium bromide (37.73 g,0.10 mol), 30% sodium methoxide solution (63.03 g,0.35 mol) prepared in example 1, and 150mL of chlorobenzene as a solvent at room temperature. Dropwise adding a toluene solution of 2-amino-2, 3-dimethylbutyramide (16.93 g,0.13 mol) under stirring, heating to 60 ℃ after the dropwise adding, and preserving heat for 2 hours; after the reaction, the mixture was cooled to room temperature, diluted with water and separated to obtain a water phase. The aqueous phase was acidified with hydrochloric acid at ph=3, and filtered and dried to give 26.6g of an imidazolinone compound (I) as a white solid, the content of which was 97.2%, and the yield was 84.7%.
Comparative example 1
Methyl 5-bromomethylpyridine-2, 3-diformate (28.81 g,0.1 mol) dichloroethane solution is heated to 50 ℃, trimethylamine (6.50 g,0.11 mol) methanol solution (received by dilute hydrochloric acid as tail gas) is added dropwise into the reaction system, the temperature is kept for 3 hours after the dropwise addition, the solid is obtained by cooling and filtering, the content is 96.0% and the yield is 87.1%. LC-MS [ M ]] + ＝267.20。
Comparative example 2
To the reaction flask was added 1- (5, 6-dimethoxycarbonylpyridine-3-methyl) -N, N, N-trimethylammonium bromide (34.72 g,0.10 mol) obtained in comparative example 1, 30% sodium methoxide solution (63.03 g,0.35 mol) and toluene as a solvent 150mL at room temperature. Dropwise adding a toluene solution of 2-amino-2, 3-dimethylbutyramide (16.93 g,0.13 mol) under stirring, heating to 65 ℃ after the dropwise adding (a large amount of trimethylamine is released from tail gas in the reaction process, and the tail gas is absorbed by dilute hydrochloric acid to prevent the influence on the environment), and carrying out heat preservation reaction for 2 hours; after the reaction, the mixture was cooled to room temperature, diluted with water and separated to obtain a water phase. The aqueous phase was acidified with hydrochloric acid at ph=3, and filtered and dried to give 25.8g of an imidazolinone compound (I) as a white solid, the content of which was 96.5%, and the yield was 81.6%.
Claims (10)
1. An intermediate for the preparation of an imidazolinone compound (I), characterized by: the intermediate has the following structure
In the method, in the process of the invention,
R 1 、R 2 independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, phenyl, halophenyl, phenyl C 1 -C 6 Alkyl or halophenyl C 1 -C 6 An alkyl group;
x is selected from chlorine or bromine;
Q + selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 3 -C 6 Cycloalkyl C 1 -C 6 Alkyl, C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, C 1 -C 6 Alkyldi (oxy C) 1 -C 6 Alkyl group, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl NR 3 R 4 。
2. An intermediate for the preparation of an imidazolinone compound (I) according to claim 1, characterized in that: in the case of the intermediate body type, the intermediate body,
R 1 、R 2 independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl;
x is selected from bromine;
Q + selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 An alkyl group.
3. Use of an intermediate for the preparation of an imidazolinone compound (I) according to claim 1, characterized in that: the use of said intermediate compounds for the preparation of imidazolinone compounds.
4. A process for producing an imidazolinone compound (I), characterized by: the reaction is that
In the general formula II
R 1 、R 2 Independently of one another, may be identical or different and are selected from C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, phenyl, halophenyl, phenyl C 1 -C 6 Alkyl or halophenyl C 1 -C 6 An alkyl group;
wherein X is selected from chlorine or bromine;
q in + Selected from the following groups:
R 3 、R 4 independently of one another, may be the same or different and are selected from hydrogen, C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 3 -C 6 Cycloalkyl C 1 -C 6 Alkyl, C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, phenyl;
R 5 selected from C 1 -C 6 Alkyl hydroxy, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl, C 1 -C 6 Alkyldi (oxy C) 1 -C 6 Alkyl group, C 1 -C 6 Alkyloxy C 1 -C 6 Alkyl NR 3 R 4 。
5. A process for preparing an imidazolinone compound (I) according to claim 4, wherein: adding a compound of the general formula III into a solvent A, dropwise adding an alcohol solution of an amine base Q in the range from 0 ℃ to the boiling point of the solvent A, and reacting to obtain a quaternary ammonium salt compound of the general formula II; reacting a quaternary ammonium salt compound with 2-amino-2, 3-dimethylbutyramide in a solvent B at 0 ℃ in the presence of alkali and within the boiling point range of the solvent B, and acidifying after the reaction to obtain an imidazolinone compound (I); wherein the mass ratio of the amine base Q to the alcohol in the alcohol solution of the amine base Q is 1:0.5-3.5, and the selection of the Q in the amine base Q is consistent with the description in the general formula.
6. A process for preparing an imidazolinone compound (I) according to claim 5, wherein:
the alcohol is selected from methanol, ethanol, isopropanol and tert-butanol; the solvent A is selected from one or more of dichloromethane, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene or dichlorobenzene;
the alkali is selected from sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide or potassium tert-butoxide; the acid is one or more of hydrochloric acid, sulfuric acid and acetic acid; the solvent B is one or more selected from methanol, ethanol, isopropanol, tertiary butanol, dichloromethane, carbon tetrachloride, dichloroethane, toluene, chlorobenzene or dichlorobenzene.
7. A process for preparing an imidazolinone compound (I) according to claim 5 or 6, wherein: the compound shown in the general formula III is added into excessive solvent A at the temperature of between 0 ℃ and the boiling point range of the solvent A, then an alcohol solution of amine base Q is added dropwise, salification reaction is carried out for 0.5 to 10 hours, and the compound shown in the general formula II is obtained by filtration; wherein the molar ratio of the compound shown in the general formula III to the amine base Q is 1:1-1.5.
8. The process for producing an imidazolinone compound (I) according to claim 7, wherein: the compound shown in the general formula III is added into excessive solvent A at the temperature of 20 ℃ to the boiling point range of the solvent A, then an alcohol solution of amine base Q is added dropwise, salification reaction is carried out for 0.5-6 hours, and the compound shown in the general formula II is obtained by filtration; wherein the molar ratio of the compound shown in the general formula III to the amine base Q is 1:1-1.3;
the alcohol is selected from methanol, ethanol and isopropanol; the solvent A is selected from carbon tetrachloride, chloroform, dichloroethane and chlorobenzene.
9. A process for preparing an imidazolinone compound (I) according to claim 5, wherein: the quaternary ammonium salt compound shown in the general formula II and 2-amino-2, 3-dimethylbutyramide are subjected to condensation reaction in an excessive solvent B in the presence of alkali at the temperature of 0 ℃ to the boiling point range of the solvent B for 0.5-10 hours, and then acidized to obtain an imidazolinone compound (I); wherein,,
the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the 2-amino-2, 3-dimethylbutyramide is 1:1-1.5; the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the alkali is 1:2-5.
10. A process for preparing an imidazolinone compound (I) according to claim 9, characterized in that: the quaternary ammonium salt compound shown in the general formula II and 2-amino-2, 3-dimethylbutyramide are subjected to condensation reaction in an excessive solvent B in the presence of alkali at the temperature of 20 ℃ to the boiling point range of the solvent B for 0.5-8 hours, and then acidized to obtain an imidazolinone compound (I); wherein the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the 2-amino-2, 3-dimethylbutyramide is 1:1-1.2; the molar ratio of the quaternary ammonium salt compound shown in the general formula II to the alkali is 1:3-4; the solvent B is selected from dichloroethane, toluene or chlorobenzene, and the base is selected from sodium methoxide, potassium methoxide or sodium ethoxide; the acid is selected from hydrochloric acid or sulfuric acid.
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