CN110698421B - Synthesis method of benzoxazolone - Google Patents
Synthesis method of benzoxazolone Download PDFInfo
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- CN110698421B CN110698421B CN201911288808.3A CN201911288808A CN110698421B CN 110698421 B CN110698421 B CN 110698421B CN 201911288808 A CN201911288808 A CN 201911288808A CN 110698421 B CN110698421 B CN 110698421B
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- benzoxazolone
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- aminophenol
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- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000001308 synthesis method Methods 0.000 title description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 27
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 9
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 15
- 239000004202 carbamide Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010189 synthetic method Methods 0.000 claims 1
- 238000004811 liquid chromatography Methods 0.000 abstract description 8
- 239000002699 waste material Substances 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000012768 molten material Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000009286 beneficial effect Effects 0.000 description 5
- 238000009776 industrial production Methods 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 4
- -1 2-hydroxy-phenylamino Chemical group 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- ZJVCOTXHMRUAIW-UHFFFAOYSA-N 3h-1,3-benzoxazol-2-one Chemical compound C1=CC=C2OC(=O)NC2=C1.C1=CC=C2OC(=O)NC2=C1 ZJVCOTXHMRUAIW-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000830535 Ligustrum lucidum Species 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention relates to the technical field of organic synthesis, in particular to a method for continuously synthesizing benzoxazolone in a horizontal double-spiral reactor in a molten state. Compared with the traditional solvent-free method, the method has the advantages that the reaction device is a horizontal double-helix reactor, the method is continuous, uniform in heating, good in stirring effect, short in reaction time and the like, the atomic utilization rate of the product is high, the yield is 97.3-98.5% (calculated by 2-aminophenol), the content is 98.3-99.1% (liquid chromatography, external standard), the amount of three wastes is small, the method is easy to process, the operation is simple, and the automatic production is facilitated.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a continuous method for synthesizing benzoxazolone in a solvent-free system.
Background
The benzoxazolone (Benzoxazolinone) is a light yellow solid in appearance and has a melting point of 140-142 ℃. The molecular formula is as follows: c7H5NO2Molecular weight: 135.12, molecular structural formula:
the chemical properties of the benzoxazolone are relatively active, for example, the hydrogen atom on the 3-position in the molecular structural formula can perform hydroxymethylation reaction with formaldehyde, the hydrogen on the 6-position of a benzene ring is easily replaced by chlorine, and the benzoxazolone can be easily subjected to ring opening in a strong alkaline medium to generate 2-hydroxy-phenylamino and the like. These properties make benzoxazolones an important use in pesticides, medicine and other fields. In the aspect of pesticides, benzoxazolone is an important intermediate of high-efficiency low-toxicity herbicide such as fenoxaprop-P-ethyl and metamifop, and pesticide such as vozapyr, and the benzoxazolone can be used for producing various analgesics, hypnotics and antipyretics in the aspect of medicine, and the following methods are mainly reported at present.
CN105669477 discloses a method for high-temperature cyclization of 2-aminophenol and urea in 48% sulfuric acid water solution, although the by-product ammonia gas generated in the reaction can be directly absorbed by dilute acid, the corrosion of strong acid medium at high temperature to equipment is serious, and three wastes are more, which is not beneficial to environmental protection.
Yuanli et al (synthesis and biological activity of N-substituted benzoxazolinone and N-substituted benzoxazolinone compounds [ J ] modern pesticides 2009, 8(01): 15-19) report a method for preparing benzoxazolone by using 2-aminophenol and solid phosgene, and although the method has the advantages of simple operation, high yield and the like, the method has the disadvantages that solid phosgene with high toxicity is used, and corrosive gas as a byproduct corrodes equipment seriously, thus being not beneficial to industrial production.
CN1398857 discloses a method for synthesizing benzoxazolone from 2-nitrophenol and carbon monoxide, which reduces the use of toxic substances such as phosgene, but the reaction catalyst is selenium powder, and the catalytic reaction is carried out under high pressure, requiring special equipment; although the subsequent improvement makes the catalytic reaction proceed under normal pressure, the product is purified by column chromatography, and the disadvantages of low yield and the like are not improved, so that the method is not suitable for industrial production.
CN 108794421 discloses a method for synthesizing benzoxazolone from 2-aminophenol and urea in DMF at high temperature, but the purification method is column chromatography, the yield is low, the operation is complex, and is not beneficial to industrial production, and organic solvent is used, and a large amount of organic waste liquid is generated.
Ligustrum lucidum (review of benzoxazolone synthesis methods [ J ]. Hunan chemical industry, 1994, (03): 14-17.) reports a traditional method for synthesizing benzoxazolone in a solvent-free system, wherein 2-aminophenol and urea are added into a three-neck flask, and then the temperature is gradually increased from low to high, so that the mixture reacts in a molten state to obtain the benzoxazolone. Although the method reduces the use of organic solvents, the temperature is high, the reaction time is long, the color of the product is dark, further decolorization treatment is needed, and the yield is only 82%.
Disclosure of Invention
The invention mainly aims to overcome the problems that an organic solvent system is used in the traditional benzoxazolone synthesis process, which is not beneficial to environmental protection and the like, and provides a continuous synthesis method of benzoxazolone in a solvent-free system, wherein the method has mild reaction conditions and small corrosion to equipment; the post-treatment is simple, the reaction liquid is only required to be transferred into hot water for cooling, crystallization, filtration and drying, the reaction and the post-treatment have continuity, the operation procedures are reduced, and the waste materials generated in industrial production are greatly reduced due to the fact that no organic solvent is used in a reaction system, so that the whole process is more environment-friendly.
In order to achieve the purpose, the invention adopts the following technical scheme:
continuously adding 2-aminophenol and urea at a certain temperature in a horizontal double-spiral reactor with the relative vacuum degree of-0.01 MPa to-0.02 MPa according to a fixed proportion, reacting the reaction materials in the reactor under the spiral push, timely removing the generated ammonia gas by negative pressure air suction, continuously transferring the reaction materials to hot water, cooling and crystallizing, filtering and drying to obtain the benzoxazolone.
The reaction formula is as follows:
the invention adopts a continuous method to synthesize the benzoxazolone by the 2-aminophenol and the urea, does not use organic solvent in the reaction and post-treatment processes, effectively reduces the problems of raw material cost, VOCs and the like in three wastes, has mild and easily-controlled continuous reaction conditions and high product quality and yield, and has important significance for industrial production.
Preferably, the molar ratio of 2-aminophenol to urea is controlled during the reaction between 1:1.1 to 1.5. The conversion rate and yield of the reaction in the molar ratio are better, the by-products are less, and when the molar ratio of the 2-aminophenol to the urea is less than 1:1.1, the 2-aminophenol is remained.
Preferably, the relative degree of vacuum in the horizontal double-screw reactor is set to-0.01 MPa to-0.02 MPa. The negative pressure is more beneficial to removing the by-product ammonia gas out of the reaction system from distillation and condensation, and the reaction process is accelerated.
Preferably, the reaction temperature is controlled to be 120-150 ℃ in the reaction process. The reaction is more complete and byproducts are less in the temperature range, and when the reaction temperature is lower than 120 ℃, more 2-aminophenol remains and the conversion rate is low; and when the temperature is higher than 150 ℃, the color of the product is darkened, and the content is reduced, so that the temperature must be strictly controlled to be 120-150 ℃ to ensure that the yield and the content of the product are high.
Preferably, the reaction time is controlled within 0.5-1 h, the conversion rate of the raw materials in the reaction time is relatively high, and the quality of the product can be ensured.
Preferably, the temperature of the hot water is 50-90 ℃, the solid particles of the cooling crystallization are relatively uniform in the temperature range, and the solid particles of the cooling crystallization are relatively large when the temperature is lower than 50 ℃, and even the caking phenomenon affects the product quality.
Preferably, the mass of the hot water used is 1 time or more of that of the 2-aminophenol, and when the mass is less than 1 time, the cooled and crystallized solid is viscous, the stirring effect is poor, and the content is low.
Preferably, the cooling crystallization temperature is 10-30 ℃, the solid content and yield of the crystals in the temperature range are high, the temperature is lower than 10 ℃, the content of the product is lower, and the yield is slightly lower when the temperature is higher than 30 ℃.
Compared with the prior art, the invention has the advantages that:
1) the reactor is a horizontal double-helix reactor, the materials are heated uniformly, the stirring effect is good, and the reaction time is convenient to control;
2) the product content is high and is 98.3-99.1% (liquid chromatography, external standard);
3) the yield is high and is 97.3 to 98.5 percent (calculated by 2-aminophenol);
4) the post-treatment is simple, the reaction process and the post-treatment are continuous, the quality is stable, and the automatic production is convenient;
5) organic solvent is not used in the reaction system, the amount of three wastes is small, and the treatment is easy, so that the whole process is more environment-friendly;
6) the generated ammonia gas can be absorbed by sulfuric acid to prepare byproducts such as ammonium sulfate and the like.
Detailed Description
Example 1:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.02 MPa), the temperature is raised to 120 ℃, 660.0g (6.05 mol) of 2-aminophenol and 399.6g (6.66 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 1h, and the generated ammonia gas is removed out of the system in time. The reaction material is transferred into 1320.0g of 90 ℃ water while the reaction material is hot, is continuously stirred for 30min, is cooled to 30 ℃, is filtered and dried to obtain 795.1g of benzoxazolone with the content of 99.1 percent (external standard of liquid chromatography) and the yield of 97.3 percent (calculated by 2-aminophenol).
Example 2:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.01 MPa), the temperature is raised to 150 ℃, 660.0g (6.05 mol) of 2-aminophenol and 435.9g (7.26 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 0.5h, and the generated ammonia gas is removed out of the system in time. The reaction mass is transferred into 660.0g of 50 ℃ water while hot, is continuously stirred for 30min, is cooled to 20 ℃, is filtered and dried to obtain 803.3g of benzoxazolone with the content of 98.7 percent (external standard of liquid chromatography) and the yield of 98.3 percent (calculated by 2-aminophenol).
Example 3:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.01 MPa), the temperature is raised to 120 ℃, 660.0g (6.05 mol) of 2-aminophenol and 544.9g (9.07 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 0.8h, and the generated ammonia gas is removed out of the system in time. The reaction mass is transferred into 1320.0g of 70 ℃ water while hot, is continuously stirred for 30min, is cooled to 10 ℃, is filtered and dried to obtain 804.9g of benzoxazolone with the content of 98.9 percent (external standard of liquid chromatography) and the yield of 98.5 percent (calculated by 2-aminophenol).
Example 4:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.02 MPa), the temperature is raised to 140 ℃, 660.0g (6.05 mol) of 2-aminophenol and 472.2g (7.86 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 0.6h, and the generated ammonia gas is removed out of the system in time. The reaction mass is transferred into 1000.0g of water with the temperature of 80 ℃ while the reaction mass is hot, the mixture is continuously stirred for 30min, cooled to 30 ℃, filtered and dried to obtain 799.2g of benzoxazolone with the content of 98.3 percent (external standard of liquid chromatography) and the yield of 97.8 percent (calculated by 2-aminophenol).
Example 5:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.02 MPa), the temperature is raised to 130 ℃, 660.0g (6.05 mol) of 2-aminophenol and 508.5g (8.47 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 0.7h, and the generated ammonia gas is removed out of the system in time. The reaction mass is transferred into 800.0g of 90 ℃ water while hot, is continuously stirred for 30min, is cooled to 20 ℃, is filtered and dried to obtain 802.5g of benzoxazolone with the content of 99.1 percent (external standard of liquid chromatography) and the yield of 98.2 percent (calculated by 2-aminophenol).
Example 6:
the rotating speed of a 2000mL horizontal double-helix reactor is controlled well, the system is under negative pressure (the relative vacuum degree is-0.01 MPa), the temperature is raised to 120 ℃, 660.0g (6.05 mol) of 2-aminophenol and 435.9g (7.26 mol) of urea are continuously added into the horizontal double-helix reactor according to the proportion, the average residence time of the molten materials in the reactor is 0.9h, and the generated ammonia gas is removed out of the system in time. The reaction mass is transferred into 1320.0g of 60 ℃ water while hot, is continuously stirred for 30min, is cooled to 30 ℃, is filtered and dried to obtain 800.8g of benzoxazolone with the content of 98.7 percent (external standard of liquid chromatography) and the yield of 98.0 percent (calculated by 2-aminophenol).
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above-described embodiments. All technical schemes belonging to the idea of the invention belong to the protection scope of the invention. It should be noted that modifications and embellishments within the scope of the invention may be made by those skilled in the art without departing from the principle of the invention, and such modifications and embellishments should also be considered as within the scope of the invention.
Claims (5)
1. A synthetic method of benzoxazolone is characterized in that: continuously adding 2-aminophenol and urea into a horizontal double-spiral reactor with the relative vacuum degree of-0.01 MPa to-0.02 MPa, controlling the reaction temperature at 120-150 ℃, transferring the reaction materials into water at 50-90 ℃ after the reaction in the reactor under the spiral pushing, cooling and crystallizing, filtering and drying to obtain the benzoxazolone.
2. The method for synthesizing benzoxazolone according to claim 1, characterized in that the molar ratio of 2-aminophenol to urea is controlled between 1:1.1 to 1.5.
3. The method for synthesizing benzoxazolone according to claim 1, characterized in that the reaction time is 0.5-1 h.
4. The method for synthesizing benzoxazolone according to claim 1, characterized in that the mass of water is more than 1 time of the mass of 2-aminophenol.
5. The method for synthesizing benzoxazolone according to claim 1, characterized in that the cooling crystallization temperature is 10-30 ℃.
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| CN1398857A (en) * | 2002-07-31 | 2003-02-26 | 中国科学院大连化学物理研究所 | Synthesis of benzoxazolinone |
| CN105669477A (en) * | 2016-03-14 | 2016-06-15 | 九江善水科技有限公司 | Method for producing 5-nitro-2aminophenol |
| CN108794421A (en) * | 2018-08-16 | 2018-11-13 | 陈万通 | The method for preparing 2- Lv benzoxazoles and 2,6- dichloro benzoxazoles from o-aminophenol as chlorinating agent using Solid triphosgene |
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