CN113105412A - Method for synthesizing benzothiazole compound - Google Patents
Method for synthesizing benzothiazole compound Download PDFInfo
- Publication number
- CN113105412A CN113105412A CN202110243046.6A CN202110243046A CN113105412A CN 113105412 A CN113105412 A CN 113105412A CN 202110243046 A CN202110243046 A CN 202110243046A CN 113105412 A CN113105412 A CN 113105412A
- Authority
- CN
- China
- Prior art keywords
- benzothiazole compounds
- reaction
- synthesizing
- benzothiazole
- crude
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 20
- -1 benzothiazole compound Chemical class 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 12
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000012544 monitoring process Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 238000004809 thin layer chromatography Methods 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 241000282414 Homo sapiens Species 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- NGIRMPARLVGMPX-UHFFFAOYSA-N 2-amino-4-chlorobenzenethiol Chemical compound NC1=CC(Cl)=CC=C1S NGIRMPARLVGMPX-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical group CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CVULGJIRGZVJHQ-UHFFFAOYSA-N 2-ethylbenzothiazole Chemical compound C1=CC=C2SC(CC)=NC2=C1 CVULGJIRGZVJHQ-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 description 1
- FHNDWGLSMGUUPO-UHFFFAOYSA-N 5-chloro-2-ethyl-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(CC)=NC2=C1 FHNDWGLSMGUUPO-UHFFFAOYSA-N 0.000 description 1
- XCALAYIRFYALSX-UHFFFAOYSA-N 5-chloro-2-methyl-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(C)=NC2=C1 XCALAYIRFYALSX-UHFFFAOYSA-N 0.000 description 1
- SVTDXKPYBJXBJR-UHFFFAOYSA-N 5-chloro-2-phenyl-1,3-benzothiazole Chemical compound N=1C2=CC(Cl)=CC=C2SC=1C1=CC=CC=C1 SVTDXKPYBJXBJR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention relates to a novel process for synthesizing benzothiazole compounds, which comprises the following steps: heating and stirring original acid ester, o-amino thiophenol and derivatives thereof for reaction, monitoring the reaction process by TLC (thin layer chromatography), and obtaining a crude product of benzothiazole compounds after the reaction is finished; the method comprises the step of distilling crude benzothiazole compounds or recrystallizing the crude benzothiazole compounds by using a solvent, and filtering the crude benzothiazole compounds to obtain the benzothiazole compounds. In the method, no solvent is added in the reaction process, the separation and purification process is optimized, and the green production of fine chemicals is effectively realized; no catalyst is added, the operation is simple, the reaction time is obviously shortened, the production efficiency of the product is improved, and the yield can reach 79-90%. The problems of environmental pollution, potential safety hazard, harm to human health, resource waste and the like caused by the solvent are fundamentally solved, and the method has strong green industrialization value.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a synthesis method of a benzothiazole compound.
Background
Benzothiazole is a representative nitrogen-containing heterocycle, widely exists in various natural compounds, is widely used as an antioxidant, a plant growth regulator, an imaging agent, a fluorescent material, an electroluminescent device and the like due to high biological and pharmacological activities, and can be used as a core structural unit for designing drug molecules with anticancer, antibacterial, antitubercular, antidiabetic, anthelmintic, antitumor, antiviral, antioxidant, anti-inflammatory, anticonvulsant and the like.
With the social development, the environmental protection problem is emphasized by people, and the search for a clean and efficient organic synthesis method becomes an important challenge in the field of heterocyclic compound preparation. Organic solvents and various catalysts are usually added in the traditional synthesis method, but most of the organic solvents have the defects of toxicity, strong pungent smell, flammability, corrosiveness, easiness in volatilization and the like; and the use of part of metal catalysts may cause heavy metal pollution, which brings serious harm to human beings, animals, plants and living environment thereof.
Because the preparation methods in the prior patents and related documents have defects and shortcomings, which are not in accordance with the green chemistry and atom economy concepts, the healthy and sustainable development of the products is influenced. Therefore, the development of a solvent-free and catalyst-free green synthesis method of the benzothiazole compounds has important practical significance.
Disclosure of Invention
The invention aims to provide a method for synthesizing benzothiazole compounds.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for synthesizing benzothiazole compounds, which is characterized by comprising the following steps:
in the structural formula R1Can be one of a plurality of substituent groups such as hydrogen ions, halogen atoms and the like, wherein the halogen atoms are chlorine atoms; r2Is one of various substituent groups such as hydrogen ion, methyl, ethyl, phenyl and the like.
Specifically, the synthesis is carried out by a melting method without adding a solvent and a catalyst.
Heating and stirring ortho-acid ester, o-aminothiophenol and derivatives thereof for reaction, monitoring the reaction process by TLC, and obtaining a crude product of benzothiazole compounds after the reaction is finished; (2) and (2) distilling the crude product of the benzothiazole compound obtained in the step (1) or recrystallizing by using a solvent, and filtering to obtain the product of the benzothiazole compound.
The molar ratio of the orthoester and the o-aminothiophenol in the step (1) is 1.2:1, and the reaction temperature is 70-90 ℃.
The recrystallization solvent used in the step (2) is ethanol and water.
The orthoester is triethyl orthoformate, triethyl orthoacetate, triethyl orthopropionate, or triethyl orthobenzoate.
The derivatives of o-aminothiophenol include o-aminothiophenol and 2-amino-4-chlorobenzenethiol.
The invention has the following advantages and positive effects:
the invention opens up a new process for synthesizing benzothiazole compounds without solvent and catalyst, no solvent is added in the reaction process, the separation and purification process is optimized, and the green production of fine chemicals is effectively realized; no catalyst is added, the operation is simple, the reaction time is obviously shortened, the production efficiency of the product is improved, and the yield can reach 79-90%. The problems of environmental pollution, potential safety hazard, harm to human health, resource waste and the like caused by the solvent are fundamentally solved, and the method has strong green industrialization value.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the present invention will be further described in detail with reference to the following preferred embodiments.
Example 1:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.25g of o-aminothiophenol and 1.78g of triethyl orthoformate, heated to 70 ℃ and subjected to an open reaction for 4 hours, and the progress of the reaction was checked by TLC. After the reaction was complete, the benzothiazole was distilled as a pale yellow liquid with a yield of 90.3%.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝8.93(s,1H),8.11(d,J＝8.0Hz,1H),7.88(dt,J＝8.0Hz,1H),7.49–7.41(m,1H),7.40–7.32(m,1H)。
example 2:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.25g of o-aminothiophenol and 1.94g of triethyl orthoacetate, heated to 70 ℃ and subjected to an open reaction for 5 hours, and the progress of the reaction was checked by TLC. When the reaction is complete, the 2-methylbenzothiazole is distilled to obtain a light yellow liquid, and the yield is 85.6%.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝7.94(d,J＝8.2Hz,1H),7.80(d,J＝8.2Hz,1H),7.43(td,J＝8.3,1.1Hz,1H),7.32(td,J＝8.2,1.1Hz,1H),2.82(s,3H)。
example 3:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.25g of o-aminothiophenol and 2.11g of triethyl orthopropionate, heated to 80 ℃ to carry out an open reaction for 5 hours, and the progress of the reaction was checked by TLC. When the reaction is complete, the 2-ethylbenzothiazole is obtained by distillation as a light yellow liquid, and the yield is 83.2 percent.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝7.95(dt,J＝8.2,0.9Hz,1H),7.82–7.75(m,1H),7.41(ddd,J＝8.3,7.2,1.3Hz,1H),7.29(ddd,J＝8.2,7.2,1.2Hz,1H),3.11(q,J＝7.6Hz,2H),1.43(t,J＝7.6Hz,3H)。
example 4:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round bottom flask was charged with 1.25g of o-aminothiophenol and 2.69g of triethyl orthobenzoate, heated to 70 ℃ to effect an open reaction for 4 hours, and the progress of the reaction was checked by TLC. After the reaction is complete, recrystallizing by using an ethanol/water system, and filtering to obtain light yellow solid 2-phenylbenzothiazole with the yield of 88.6 percent; melting point 113 ℃ and 114 ℃.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝8.09(m,3H),7.91(d,J＝8.0Hz,1H),7.50(m,4H),7.39(td,J＝7.1,1.2Hz,1H)。
example 5:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.59g of 2-amino-4-chlorobenzenethiol and 1.78g of triethyl orthoformate, heated to 70 ℃ to effect an open reaction for 4.5 hours, and the progress of the reaction was checked by TLC. After the reaction is complete, ethanol/water system is used for recrystallization, and light yellow solid 5-chlorobenzo [ d ] thiazole is obtained by filtration, wherein the yield is 85.3%; the melting point is 40-42 ℃.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝9.02(s,1H),8.12(s,1H),7.85(d,J＝9.0Hz 1H),7.43(d,J＝9.0Hz,1H)。
example 6:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.59g of 2-amino-4-chlorobenzenethiol and 1.94g of triethyl orthoacetate, heated to 80 ℃ to effect an open reaction for 6 hours, and the progress of the reaction was checked by TLC. After the reaction is complete, ethanol/water system is used for recrystallization, and light yellow solid 5-chloro-2-methylbenzo [ d ] thiazole is obtained by filtration, wherein the yield is 83.1%; the melting point is 68-70 ℃.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝7.93(s,1H),7.73(d,J＝8.5Hz,1H),7.33(dd,J＝8.5,2.0Hz,1H),2.84(s,3H)。
example 7:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.59g of 2-amino-4-chlorobenzenethiol and 2.11g of triethyl orthopropionate, heated to 90 ℃ to carry out an open reaction for 6 hours, and the progress of the reaction was checked by TLC. After the reaction is complete, ethanol/water system is used for recrystallization, and light yellow solid 5-chloro-2-ethylbenzo [ d ] thiazole is obtained by filtration, wherein the yield is 79.8%; the melting point is 55-57 ℃.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝7.93(d,J＝2.0Hz,1H),7.73(d,J＝8.5Hz,1H),7.29–7.34(m,1H),3.14(q,J＝7.6Hz,2H),1.46(t,J＝7.6Hz,3H)。
example 8:
a method for synthesizing benzothiazole compounds comprises the following steps:
a25 mL round-bottom flask was charged with 1.59g of 2-amino-4-chlorobenzenethiol and 2.69g of triethyl orthobenzoate, heated to 80 ℃ to effect an open reaction for 5 hours, and the progress of the reaction was checked by TLC. After the reaction is complete, ethanol/water system is used for recrystallization, and light yellow solid 5-chloro-2-phenylbenzo [ d ] thiazole is obtained by filtration, wherein the yield is 83.4%; melting point 137-139 ℃.
And (3) detecting a product:1H NMR(400MHz,CDCl3)δ＝8.10–7.98(m,3H),7.81(d,J＝8.5Hz,1H),7.48–7.53(m,3H),7.34–7.38(m,1H)。
Claims (6)
1. a method for synthesizing benzothiazole compounds is characterized by comprising the following steps: the reaction formula is as follows:
wherein R is1Is a hydrogen ion or a halogen atom, R2Is hydrogen ion, methyl, ethyl or phenyl.
2. The method for synthesizing benzothiazole compounds according to claim 1, wherein: the halogen atom is a chlorine atom.
3. The method for synthesizing a benzothiazole compound according to claim 1, wherein the synthesis is performed by a melt method without adding a solvent or a catalyst.
4. The method for synthesizing a benzothiazole compound according to claim 1, wherein: the method comprises the following specific steps:
heating and stirring original acid ester, o-amino thiophenol and derivatives thereof for reaction, monitoring the reaction process by TLC (thin layer chromatography), and obtaining a crude product of benzothiazole compounds after the reaction is finished;
the method comprises the step of distilling crude benzothiazole compounds or recrystallizing the crude benzothiazole compounds by using a solvent, and filtering the crude benzothiazole compounds to obtain the benzothiazole compounds.
5. The method for synthesizing benzothiazole compounds according to claim 4, wherein: the method comprises the steps that the molar ratio of the ortho-stearic acid ester to the ortho-amino thiophenol and the derivatives thereof is 1.2:1, and the reaction temperature is 70-90 ℃.
6. The method for synthesizing benzothiazole compounds according to claim 4, wherein: in the step II, ethanol and water are used as recrystallization solvents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110243046.6A CN113105412A (en) | 2021-03-05 | 2021-03-05 | Method for synthesizing benzothiazole compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110243046.6A CN113105412A (en) | 2021-03-05 | 2021-03-05 | Method for synthesizing benzothiazole compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113105412A true CN113105412A (en) | 2021-07-13 |
Family
ID=76710328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110243046.6A Pending CN113105412A (en) | 2021-03-05 | 2021-03-05 | Method for synthesizing benzothiazole compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113105412A (en) |
-
2021
- 2021-03-05 CN CN202110243046.6A patent/CN113105412A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107892654B (en) | Isolongifolane-based fluorescent acid-base indicator and synthetic method and application thereof | |
| CA2368815A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| NO143531B (en) | PROCEDURE FOR PREPARING ACYLATED BENZOCSAZOLINON DERIVATIVES | |
| EP3088391B1 (en) | Method for producing benzyl ester 2-aminonicotinate derivative | |
| EP0002978B1 (en) | Thiazolidinedione-2,4 derivatives, their preparation and pharmaceutical applications | |
| CN113105412A (en) | Method for synthesizing benzothiazole compound | |
| CN109320468B (en) | Method for mild preparation of benzo [ a ] phenazine compound | |
| Moghaddam et al. | Efficient and green synthesis of new polycyclic procyanidin derivatives via tandem dinucleophilic addition of indolin-2-thiones to flavylium salts | |
| CN111961011B (en) | Preparation method of C2 substituted 2H-benzothiazole hydroxyalkylated derivative | |
| JPH0116837B2 (en) | ||
| KR100406474B1 (en) | Method for producing 2- (pyrid-2-yloxymethyl) phenylacetate as an agricultural chemical intermediate | |
| US4287348A (en) | Preparation of sulphoalkyl quaternary salts | |
| CN107954960B (en) | Synthetic method of 1,3-dihydroisobenzofuran compound | |
| CN106316999B (en) | A kind of preparation method and application of two ketoximes derivatives of benzofuran -2,3- | |
| CN111377927A (en) | Thio or selenamide compound and preparation method thereof | |
| KR102292794B1 (en) | Preparation method of 2-substituted 1,2,3,4-tetrahydroquinoline compound | |
| RU2295521C2 (en) | Photochrome oxazine compounds and methods for their synthesis | |
| JPH01313457A (en) | Production of n-(3', 4'-dimethoxy-cinnamoyl)- anthranylic acid | |
| CN111892582B (en) | Preparation method of benzofuran coumarin compound | |
| DE10361794B3 (en) | Optically active heteroaromatic β-hydroxy esters and processes for their preparation and their use as intermediates in the epothilone total synthesis | |
| EP0062068B1 (en) | N-phthalidyl-5-fluorouracil derivatives | |
| CN108503582B (en) | Microwave-assisted synthesis method of 2- (1H) -quinolinone compounds | |
| DE19853558A1 (en) | Process for the preparation of 2,3-dihydroindoles (indolines), novel 2,3-dihydroindoles and their use | |
| CN110294715B (en) | Synthesis method of 2,4, 6-trichloro-5-methoxypyrimidine | |
| CN100534989C (en) | Resolving process of (RS)-benzdioxan-2-formic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |