CN117886755A - Preparation method of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate - Google Patents
Preparation method of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate Download PDFInfo
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- CN117886755A CN117886755A CN202311736782.0A CN202311736782A CN117886755A CN 117886755 A CN117886755 A CN 117886755A CN 202311736782 A CN202311736782 A CN 202311736782A CN 117886755 A CN117886755 A CN 117886755A
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- dihydroimidazole
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- -1 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate Chemical compound 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 229940015043 glyoxal Drugs 0.000 claims abstract description 7
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000071 diazene Inorganic materials 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000003756 stirring Methods 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 14
- 238000005406 washing Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 3
- AUPAYCJYILOTQL-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole Chemical compound CC1=CC(C)=CC(C)=C1N1CCN(C=2C(=CC(C)=CC=2C)C)[CH]1 AUPAYCJYILOTQL-UHFFFAOYSA-N 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 4
- 229910000510 noble metal Inorganic materials 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N beta-hydroxybutyraldehyde Natural products CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 230000009467 reduction Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 1, 3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydro imidazole tetrafluoroborate, which belongs to the technical field of preparation of noble metal catalyst ligands and comprises the following steps: s1: synthesizing diimine; s2: synthesizing a secondary amine; s3: salifying the secondary amine; s4: closing a ring by using di-secondary amine hydrochloride; s5: 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate; s6: purifying the crude product; according to the invention, glyoxal and mesitylene are used as starting materials, and 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate with the yield up to 91% is prepared through aldol amine condensation, reduction, salifying, ring closing, replacement and purification, so that the invention has the advantages of high yield, low raw material price, low manufacturing cost, and good market popularization potential and application prospect.
Description
Technical Field
The invention belongs to the technical field of noble metal catalyst ligand preparation, and particularly relates to a preparation method of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate.
Background
1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate is a noble metal catalyst ligand which can be coordinated with various noble metal pre-catalysts to synthesize corresponding catalysts, and has wide application prospect, but no perfect synthesis method can be used for producing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate with high yield in large quantities at present.
Disclosure of Invention
To solve the problems set forth in the background art. The invention provides a preparation method of 1, 3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydro imidazole tetrafluoroborate, which has the characteristics of high yield and low manufacturing cost.
In order to achieve the above purpose, the present invention provides the following technical solutions: the preparation method of the 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate comprises the following steps:
s1: synthesis of diimines
Glyoxal and mesitylene are used as raw materials, methanol is used as a solvent, stirring reaction is carried out for 24 hours at room temperature, solid is separated out, then the solid is filtered, washed by ethanol for three times, and vacuum drying is carried out, thus obtaining a bright yellow solid;
s2: synthesis of a Di-secondary amine
Taking the synthesized diimine, sodium dithionite and sodium hydroxide as raw materials, taking ethanol as a solvent, reacting for 24 hours at the temperature of 40 ℃, removing the ethanol by vacuum rotary evaporation, adding dichloromethane to extract twice, removing water from a dichloromethane layer by anhydrous sodium sulfate, and concentrating by rotary evaporation to obtain colorless transparent oily matter;
s3: salt formation of a secondary amine
Stirring and dissolving the synthesized secondary amine with dichloromethane at room temperature, dropwise adding concentrated hydrochloric acid into the solution in the stirring process to carry out salt formation reaction, continuously stirring for 30min, filtering white precipitate, washing the solid with dichloromethane twice, and drying in vacuum to obtain a white solid;
s4: di-secondary amine hydrochloride ring closure
Adding trimethyl orthoformate and formic acid into the prepared di-secondary amine hydrochloride, stirring at 100 ℃ for reaction for 5 hours, cooling to room temperature, adding petroleum ether with the same volume as the trimethyl orthoformate into the mixture, stirring, standing, filtering, washing with petroleum ether twice, and vacuum drying to obtain white solid;
s5: substituted with 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate
Adding tetrahydrofuran into the prepared di-secondary amine hydrochloride, stirring for dissolving, dripping 50% fluoboric acid aqueous solution at room temperature to react in the stirring process, continuously stirring for 30min, filtering the white solid, washing the solid twice with water, and vacuum drying to obtain 1, 3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydroimidazole tetrafluoroborate;
s6: purifying the crude product
And (3) stirring and dissolving the prepared crude 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate with methanol at room temperature, adding dichloromethane into the stirring process to react, continuously stirring for 30min, filtering, washing a white filter cake twice with ethyl glacial acetate, and drying in vacuum to obtain a pure product of the 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate.
Further, in the step S1, the addition molar ratio of glyoxal to mesitylene is 2:1, and the addition amounts of methanol and ethanol are 300mL and 200mL respectively.
Further, in the step S2, the molar ratio of the diimine, sodium dithionite and sodium hydroxide is 1:4:8, the addition amounts of ethanol and methylene chloride of the aqueous solution with the sodium hydroxide concentration of 0.2M are 200mL and 200mL respectively.
Further, in the step S3, the addition amount of methylene chloride was 10 times by mass volume of the secondary amine, the addition amount of concentrated hydrochloric acid was 3 equivalents, and the addition amount of methylene chloride was 100mL.
Further, in the step S4, the addition amount of trimethyl orthoformate was 5 times the mass volume of the di-sec-amine hydrochloride, the addition amount of formic acid was 3 drops, and the addition amounts of stirring petroleum ether and washing petroleum ether were 125mL and 100mL, respectively.
Further, in the step S5, the amount of tetrahydrofuran added was 20 times by mass as much as that of the di-secondary amine hydrochloride, the amount of 50% aqueous fluoroboric acid solution added was 3 equivalents, and the amount of washing water added was 100mL.
Further, in the step S6, the addition amount of methanol is 5 times the mass volume of the crude product of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate, the addition amount of methylene chloride is 3 times the mass volume of methanol, and the addition amount of ethyl glacial acetate is 50mL.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, glyoxal and mesitylene are used as starting materials, and 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate with the yield up to 91% is prepared through aldol amine condensation, reduction, salifying, ring closing, replacement and purification, so that the invention has the advantages of high yield, low raw material price, low manufacturing cost, and good market popularization potential and application prospect.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides the following technical scheme: the preparation method of the 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate comprises the following steps:
s1: synthesis of diimines
186.4g glyoxal (1.378 mol), 100.0g mesitylene (0.689 mol) and 300mL methanol are respectively added into a 500mL single-neck flask, stirred at room temperature for reaction for 24 hours, filtered after solid precipitation, washed by 200mL ethanol for three times, and dried in vacuum to obtain 141g bright yellow solid with the yield of 70%;
s2: synthesis of a Di-secondary amine
29.2g of the synthesized diimine (0.100 mol), 69.6g of sodium dithionite (0.400 mol), 80mL of 0.2M sodium hydroxide aqueous solution (0.800 mol) and 200mL of ethanol are respectively added into a 2L three-necked flask, the reaction is carried out for 24 hours at the temperature of 40 ℃, the ethanol is removed by vacuum rotary evaporation, 200mL of dichloromethane is added for extraction, the dichloromethane layer is dehydrated by anhydrous sodium sulfate, the rotary evaporation is concentrated, and 25.2g of colorless transparent oily matter is obtained, and the yield is 85%;
s3: salt formation of a secondary amine
25g of the synthesized secondary amine (0.084 mol) and 250mL of dichloromethane are added into a 500mL single-port bottle, stirred and dissolved, 24.9g of concentrated hydrochloric acid with the mass fraction of 37% is added dropwise in the stirring process for salifying reaction, after the dropwise addition is finished, stirring is continued for 30min, white precipitate is filtered, the solid is washed by 100mL of dichloromethane, washed twice and dried in vacuum, 29.6g of white solid is obtained, and the yield is 95%;
s4: di-secondary amine hydrochloride ring closure
To a 200mL single-necked flask, 25g of the above-prepared di-secondary amine hydrochloride (0.0677 mol), 125mL of trimethyl orthoformate and 3 drops of formic acid were added, and the mixture was stirred at 100℃for reaction for 5 hours, cooled to room temperature, 125mL of petroleum ether was added to the mixture, stirred, left to stand and filtered, washed twice with 100mL of petroleum ether, and dried in vacuo to give 21.6g of a white solid with a yield of 93%;
s5: substituted with 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate
Adding 20g of the prepared di-secondary amine hydrochloride (0.058 mol) and 400mL of tetrahydrofuran into a 500mL single-port bottle, stirring for dissolution, dropwise adding 30.7g of 50% aqueous fluoboric acid solution (0.174 mol) at room temperature in the stirring process for reaction, continuing stirring for 30min after the dropwise addition, filtering the white solid, washing the solid twice by 100mL of water, and drying in vacuum to obtain 22.7g of 1, 3-bis (2, 4, 6-trimethyl) -4, 5-dihydroimidazole tetrafluoroborate crude product with the yield of 99%;
s6: purifying the crude product
To a 500mL single-neck flask, 20g of the crude 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate and 100mL of methanol prepared above were added, and the mixture was stirred and dissolved, 300mL of methylene chloride was slowly added inward during the stirring process to react, after the addition was completed, stirring was continued for 30min, filtration was performed, the white filter cake was washed with 50mL of ethyl glacial acetate, washed twice, and vacuum-dried to obtain 18.2g of pure 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate, and the yield was 91%.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
- The preparation method of 1.1,3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydro imidazole tetrafluoroborate is characterized by comprising the following steps:s1: synthesis of diiminesGlyoxal and mesitylene are used as raw materials, methanol is used as a solvent, stirring reaction is carried out for 24 hours at room temperature, solid is separated out, then the solid is filtered, washed by ethanol for three times, and vacuum drying is carried out, thus obtaining a bright yellow solid;s2: synthesis of a Di-secondary amineTaking the synthesized diimine, sodium dithionite and sodium hydroxide as raw materials, taking ethanol as a solvent, reacting for 24 hours at the temperature of 40 ℃, removing the ethanol by vacuum rotary evaporation, adding dichloromethane to extract twice, removing water from a dichloromethane layer by anhydrous sodium sulfate, and concentrating by rotary evaporation to obtain colorless transparent oily matter;s3: salt formation of a secondary amineStirring and dissolving the synthesized secondary amine with dichloromethane at room temperature, dropwise adding concentrated hydrochloric acid into the solution in the stirring process to carry out salt formation reaction, continuously stirring for 30min, filtering white precipitate, washing the solid with dichloromethane twice, and drying in vacuum to obtain a white solid;s4: di-secondary amine hydrochloride ring closureAdding trimethyl orthoformate and formic acid into the prepared di-secondary amine hydrochloride, stirring at 100 ℃ for reaction for 5 hours, cooling to room temperature, adding petroleum ether with the same volume as the trimethyl orthoformate into the mixture, stirring, standing, filtering, washing with petroleum ether twice, and vacuum drying to obtain white solid;s5: substituted with 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborateAdding tetrahydrofuran into the prepared di-secondary amine hydrochloride, stirring for dissolving, dripping 50% fluoboric acid aqueous solution at room temperature to react in the stirring process, continuously stirring for 30min, filtering the white solid, washing the solid twice with water, and vacuum drying to obtain 1, 3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydroimidazole tetrafluoroborate;s6: purifying the crude productAnd (3) stirring and dissolving the prepared crude 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate with methanol at room temperature, adding dichloromethane into the stirring process to react, continuously stirring for 30min, filtering, washing a white filter cake twice with ethyl glacial acetate, and drying in vacuum to obtain a pure product of the 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate.
- 2. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S1, the addition molar ratio of glyoxal to mesitylene is 2:1, and the addition amounts of methanol and ethanol are 300mL and 200mL respectively.
- 3. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S2, the addition mole ratio of diimine, sodium dithionite and sodium hydroxide is 1:4:8, the addition amounts of ethanol and methylene chloride of the aqueous solution with the sodium hydroxide concentration of 0.2M are 200mL and 200mL respectively.
- 4. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S3, the addition amount of methylene chloride was 10 times by mass volume of the secondary amine, the addition amount of concentrated hydrochloric acid was 3 equivalents, and the addition amount of methylene chloride was 100mL.
- 5. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S4, the addition amount of trimethyl orthoformate is 5 times the mass volume of the di-secondary amine hydrochloride, the addition amount of formic acid is 3 drops, and the addition amounts of stirring petroleum ether and washing petroleum ether are 125mL and 100mL respectively.
- 6. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S5, the amount of tetrahydrofuran added was 20 times by mass as much as that of the di-secondary amine hydrochloride, the amount of 50% aqueous fluoroboric acid solution added was 3 equivalents, and the amount of washing water added was 100mL.
- 7. The process for preparing 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate according to claim 1, wherein: in the step S6, the addition amount of methanol is 5 times of the mass volume of the crude product of 1, 3-bis (2, 4, 6-trimethyl phenyl) -4, 5-dihydroimidazole tetrafluoroborate, the addition amount of methylene dichloride is 3 times of the mass volume of methanol, and the addition amount of ethyl glacial acetate is 50mL.
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| CN202311736782.0A CN117886755A (en) | 2023-12-18 | 2023-12-18 | Preparation method of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate |
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| CN202311736782.0A CN117886755A (en) | 2023-12-18 | 2023-12-18 | Preparation method of 1, 3-bis (2, 4, 6-trimethylphenyl) -4, 5-dihydroimidazole tetrafluoroborate |
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