CN113666848A - Preparation method of o-nitrobenzenesulfonyl chloride - Google Patents
Preparation method of o-nitrobenzenesulfonyl chloride Download PDFInfo
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- CN113666848A CN113666848A CN202110947162.6A CN202110947162A CN113666848A CN 113666848 A CN113666848 A CN 113666848A CN 202110947162 A CN202110947162 A CN 202110947162A CN 113666848 A CN113666848 A CN 113666848A
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- Prior art keywords
- kettle
- reaction
- nitrobenzenesulfonyl chloride
- stirring
- temperature
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- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910001868 water Inorganic materials 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000005406 washing Methods 0.000 claims abstract description 21
- 229910052979 sodium sulfide Inorganic materials 0.000 claims abstract description 18
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011593 sulfur Substances 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000007599 discharging Methods 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 claims description 7
- 238000003825 pressing Methods 0.000 claims description 5
- 238000011085 pressure filtration Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 abstract description 4
- 238000004073 vulcanization Methods 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/18—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by reaction of sulfides with compounds having functional groups with formation of sulfo or halosulfonyl groups
Abstract
The invention relates to the technical field of production of medical intermediates, and provides a preparation method of o-nitrobenzenesulfonyl chloride, which comprises the following steps: preparing a solution, and adding water, sodium sulfide and sulfur in a predetermined molar ratio; carrying out reaction; washing and centrifuging; II, chlorination: adding hydrochloric acid, a vulcanizing material and a catalyst in a preset ratio into a reaction kettle, and stirring; raising the temperature in the reaction kettle to be above 30 ℃, introducing chlorine gas and completing chlorine gas introduction reaction under the condition that the temperature is not more than 65 ℃; then, cooling to 35-38 ℃ and discharging; thirdly, post-treatment: after the chlorination reaction is finished, putting the material into a centrifugal machine for centrifugal treatment; and drying the centrifuged material. Therefore, the preparation of the o-nitrobenzenesulfonyl chloride is realized through the working procedures of vulcanization, chlorination, post-treatment and the like. The method has the advantages of continuous production process, high production efficiency, full reaction and high product purity, and can meet the production requirements.
Description
Technical Field
The invention belongs to the technical field of production of medical intermediates, and particularly relates to a preparation method of o-nitrobenzenesulfonyl chloride.
Background
The o-nitrobenzenesulfonyl chloride is used as a medical intermediate for synthesizing drugs such as sulfanilamide and the like.
The existing production process of o-nitrobenzenesulfonyl chloride has low production efficiency and a plurality of product impurities, and is difficult to meet the use requirement.
In view of the above, the prior art is obviously inconvenient and disadvantageous in practical use, and needs to be improved.
Disclosure of Invention
Aiming at the defects, the invention aims to provide a method for preparing o-nitrobenzenesulfonyl chloride, which realizes the preparation of o-nitrobenzenesulfonyl chloride through the working procedures of vulcanization, chlorination, post-treatment and the like. The method has the advantages of continuous production process, high production efficiency, full reaction and high product purity, and can meet the production requirements.
In order to realize the purpose, the invention provides a preparation method of o-nitrobenzenesulfonyl chloride, which comprises the following steps:
first, sulfurize
1. Solution preparation
Adding water, sodium sulfide and sulfur with a preset ratio into a reaction kettle, stirring for 4 +/-0.5 hours, and precipitating for 27-33 hours at the temperature of 55 ℃; removing residues to obtain a solution; the molar ratio of the added water, the sodium sulfide and the sulfur is as follows: 6-9:2-4: 1;
2. reaction of
Adding ethanol and o-nitrochlorobenzene in a predetermined amount into a reaction kettle and stirring; when the temperature in the kettle reaches 63 ℃, dropwise adding a sodium polysulfide solution into the kettle until the content of the o-nitrochlorobenzene is lower than 5%; after the dripping is finished, preserving the heat for 1.5 plus or minus 0.1 hour;
the molar ratio of the added ethanol to the added o-nitrochlorobenzene to the added sulfur is as follows: 1-1.5: 1;
3. washing centrifuge
Transferring the reacted solution into a washing kettle; raising the temperature in the kettle to 65-70 ℃ by adopting steam or hot water and stirring for 1 hour;
then, carrying out pressure filtration by using nitrogen; then opening a liquid inlet of the washing kettle, adding 1500-1600L ethanol into the kettle, heating the temperature in the kettle to 55-70 ℃, and stirring for 2 hours; then, introducing nitrogen for filter pressing;
then adding 1000L of hot water into the washing kettle, stirring for 60 minutes at 85-95 ℃, and then transferring the materials into a centrifuge for centrifugal treatment;
di, chlorination
Adding hydrochloric acid, a vulcanizing material and a catalyst in a preset ratio into a reaction kettle, and stirring; when the temperature in the reaction kettle rises to 40-45 ℃, introducing 450 +/-30 kg of chlorine; then, cooling to 35-38 ℃ and discharging;
third, post-treatment
After the chlorination reaction is finished, putting the material into a centrifugal machine for centrifugal treatment;
and drying the centrifuged material in a boiling drying mode.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the sodium sulfide is replaced by a sodium sulfide aqueous solution with a concentration value of 20% in the solution preparation step.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the dropping time of the sodium polysulfide solution is 7-8 hours.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the purity of ethanol added in the reaction step in the solution preparation is more than or equal to 92 percent.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the pressure in the reaction kettle is not more than 0.25MPa in the nitrogen pressure filtration process.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the cooling mode in the chlorination step is water-cooled cooling.
According to the preparation method of the o-nitrobenzenesulfonyl chloride, the concentration of hydrochloric acid in the chlorination step is 22-23%.
The invention aims to provide a method for preparing o-nitrobenzenesulfonyl chloride, which realizes the preparation of the o-nitrobenzenesulfonyl chloride through the working procedures of vulcanization, chlorination, post-treatment and the like. The method has the advantages of continuous production process, high production efficiency, full reaction and high product purity, and can meet the production requirements.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. The above-mentioned directions or positions of the upper, lower, left, right, etc. are referred to in this specification for better describing the technical solution, so that the reader can understand that the practical implementation includes but is not limited to this description.
The invention provides a preparation method of o-nitrobenzenesulfonyl chloride, which comprises the following steps:
first, sulfurize
1. Solution preparation
Adding water, sodium sulfide and sulfur into a reaction kettle in predetermined amounts, stirring for 4 +/-0.5 hours, and precipitating for 27-33 hours at 55 ℃; the molar ratio of the added water, the sodium sulfide and the sulfur is as follows: 6-9:2-4: 1;
the purity of the added sodium sulfide is not less than 60%.
Then the residue is discharged, and after stirring for 0.5 hour, the precipitate is precipitated for 18 to 22 hours at the temperature of 55 ℃; then discharging the residue again;
then, the temperature in the kettle is raised to 60 ℃, the mixture is stirred for 3 +/-0.2 hours again, and then a solution is obtained after sampling and detection;
and if the content of the sodium sulfide is detected to be lower than 20%, supplementing the sodium sulfide into the kettle until the content reaches the standard.
Example (b): 3440kg of water, 1575kg of sodium sulfide and about 424kg of sulfur are added (according to the concentration of the sodium sulfide, the ratio of sodium sulfide to sulfur is 1.05 mol). Preferably, water is added to the dissolution kettle, and then the sodium sulfide is added in a stirring state. Naturally heating, stirring for 4 hours, stopping stirring, keeping the temperature at 55 ℃, and precipitating for 30 hours;
after the residue was left, stirring was stopped for 30 minutes, and the mixture was kept at 55 ℃ for 20 hours to precipitate, and then the residue was left.
Stirring and heating to 60 ℃, stirring for 3 hours, and sampling and detecting.
2. Reaction of
Adding ethanol and o-nitrochlorobenzene in a predetermined amount into a reaction kettle and stirring; when the temperature in the kettle reaches 63 ℃, dropwise adding a sodium polysulfide solution into the kettle until the content of the o-nitrochlorobenzene is lower than 5%; after the dripping is finished, preserving the heat for 1.5 plus or minus 0.1 hour;
the dripping time is preferably 7-8 hours;
the molar ratio of the added ethanol, the added o-nitrochlorobenzene and the added sulfur is as follows: 1-1.5: 1;
preferably, the purity of the added ethanol is more than or equal to 92 percent.
Example (b): 565kg of ethanol was placed in the reaction vessel. The stirring was started. Heating to 30 ℃, adding 500kg of melted o-nitrochlorobenzene into the reaction kettle in a vacuum mode, and stirring and heating to 65 ℃; and dropwise adding the sodium polysulfide solution, wherein the adding is completed within 7.5 hours, the temperature is 65-67 ℃, the later-stage temperature is slightly higher, keeping the temperature for 1.5 hours after the adding is completed, detecting that the content of the o-nitrochlorobenzene is lower than 5%, and otherwise, supplementing the sodium polysulfide solution.
3. Washing centrifuge
Transferring the reacted solution into a washing kettle; preferably, the washing kettle is opened and emptied, and the solution after reaction is transferred into the washing kettle by a pump; after the material is transferred, 50 liters of water is used for washing the pipeline and the pipeline is continuously pumped into the washing kettle by a pump, so that the pipeline is prevented from being blocked by the remained material on the line.
Raising the temperature in the kettle to 65-70 ℃ by adopting steam and stirring for 1 hour;
then, the mother liquor is pressed into a receiving tank by using nitrogen for filter pressing (the pressure in the kettle is kept to be not more than 0.25MPa in the process). And after the mother liquor is basically subjected to filter pressing, slowly emptying the washing kettle and releasing pressure.
Then opening a liquid inlet of the washing kettle, adding 1500-1600L ethanol into the kettle, heating the temperature in the kettle to 65-70 ℃, and stirring for 2 hours; then, introducing nitrogen for filter pressing; and after the mother liquor is basically subjected to pressure filtration, slowly opening the filter to empty, and relieving pressure. Transferring the ethanol solution to a temporary storage iron tank for rectification.
Preferably, the concentration of the ethanol is more than or equal to 87 percent;
sampling and detecting, wherein the thioether content is qualified when the thioether content is less than or equal to 0.5%. If not, continuing to add ethanol for washing until qualified.
Then adding 1000L of hot water into the washing kettle, stirring for 60 minutes at the temperature of 90-95 ℃, and then transferring the materials into a centrifugal machine for centrifugal treatment; the material in the centrifuge was washed with hot water during centrifugation.
And (4) allowing the centrifuged water to enter an iron tank, and pumping the water into a sewage tank for treatment after the solid carrying-out condition is detected.
Di, chlorination
Adding 3000 liters of hydrochloric acid, 450kg of vulcanizing material and 5kg of catalyst into a reaction kettle, and stirring; when the temperature in the reaction kettle rises to 40-45 ℃, introducing chlorine for 15 hours; then, cooling to 35-38 ℃ and discharging; preferably, the invention adopts water-cooled cooling
The concentration of hydrochloric acid is preferably 22-23%;
preferably, the chlorine is introduced for 15 hours, the cold water is cooled and kept at 58-59 ℃, and the chlorine is continuously introduced until the end point (the color of the material is suddenly changed into white, the sampling observation shows that few yellow sulfide particles are remained) based on the condition that the buffer bottle does not emit green, and the temperature can reach 60 ℃. And (4) gradually reducing the ammonia amount in the later period, analyzing the end point of the plate layer, and tracking and monitoring the liquid chromatogram until the end point. Circulating water is introduced to cool to 35-38 ℃ for discharging.
Preferably, the chlorine pipeline is checked firstly; the invention adopts ammonia water for leakage detection and simultaneously opens a reaction kettle tail gas recovery system. When chlorine is introduced, the steam frame is firstly opened, the steam valve is preheated, the needle valve is opened, the small chlorine cylinder is opened, the ammonia water leakage test is carried out, the chlorine amount is adjusted to normal flux after the chlorine is normal, and the pressure of the buffer tank cannot exceed 0.2 MPa.
Third, post-treatment
After the chlorination reaction is finished, putting the material into a centrifugal machine for centrifugal treatment;
after the centrifuge finishes feeding, spin-drying at medium speed for 5 minutes, starting washing, adding water at medium speed for 5 minutes, spin-drying at medium speed for 5 minutes after water supply is stopped, adding water at medium speed for washing for 5 minutes, spin-drying at high speed for 6 minutes finally, and measuring the pH value of water at the same time. Should be above 5. And finally scraping the materials by a scraper.
And drying the centrifuged material in a boiling drying mode. The drying temperature is not more than 56 ℃. The purity of the material is not lower than 98%.
And packaging, detecting and warehousing the dried materials. The packaging specification is 25 kg/bag.
In conclusion, the invention provides a preparation method of o-nitrobenzenesulfonyl chloride, which realizes the preparation of the o-nitrobenzenesulfonyl chloride through the working procedures of vulcanization, chlorination, post-treatment and the like. The method has the advantages of continuous production process, high production efficiency, full reaction and high product purity, and can meet the production requirements.
The present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof, and it should be understood that various changes and modifications can be effected therein by one skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (7)
1. The preparation method of the o-nitrobenzenesulfonyl chloride is characterized by comprising the following steps:
first, sulfurize
1. Solution preparation
Adding water, sodium sulfide and sulfur with a preset ratio into a reaction kettle, stirring for 4 +/-0.5 hours, and precipitating for 27-33 hours at the temperature of 55 ℃; removing residues to obtain a solution; the molar ratio of the added water, the sodium sulfide and the sulfur is as follows: 6-9:2-4: 1;
2. reaction of
Adding ethanol and o-nitrochlorobenzene in a predetermined amount into a reaction kettle and stirring; when the temperature in the kettle reaches 63 ℃, dropwise adding a sodium polysulfide solution into the kettle until the content of the o-nitrochlorobenzene is lower than 5%; after the dripping is finished, preserving the heat for 1.5 plus or minus 0.1 hour;
the molar ratio of the added ethanol to the added o-nitrochlorobenzene to the added sulfur is as follows: 1-1.5: 1;
3. washing centrifuge
Transferring the reacted solution into a washing kettle; raising the temperature in the kettle to 65-70 ℃ by adopting steam or hot water and stirring for 1 hour;
then, carrying out pressure filtration by using nitrogen; then opening a liquid inlet of the washing kettle, adding 1500-1600L ethanol into the kettle, heating the temperature in the kettle to 55-70 ℃, and stirring for 2 hours; then, introducing nitrogen for filter pressing;
then adding 1000L of hot water into the washing kettle, stirring for 60 minutes at 85-95 ℃, and then transferring the materials into a centrifuge for centrifugal treatment;
di, chlorination
Adding hydrochloric acid, a vulcanizing material and a catalyst in a preset ratio into a reaction kettle, and stirring; when the temperature in the reaction kettle rises to 40-45 ℃, introducing 450 +/-30 kg of chlorine; then, cooling to 35-38 ℃ and discharging;
third, post-treatment
After the chlorination reaction is finished, putting the material into a centrifugal machine for centrifugal treatment;
and drying the centrifuged material in a boiling drying mode.
2. The method for producing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the sodium sulfide is replaced with an aqueous solution of sodium sulfide having a concentration of 20% in the step of preparing the solution.
3. The method for preparing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the time period for dropping the sodium polysulfide solution is 7 to 8 hours.
4. The method for preparing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the purity of ethanol added in the reaction step in the solution preparation is not less than 92%.
5. The method for preparing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the pressure in the reaction kettle during the nitrogen pressure filtration process is not more than 0.25 MPa.
6. The method for preparing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the cooling mode in the chlorination step is water-cooled cooling.
7. The method for preparing o-nitrobenzenesulfonyl chloride according to claim 1, wherein the concentration of hydrochloric acid in said chlorination step is between 20 and 31%.
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| CN202110947162.6A CN113666848A (en) | 2021-08-18 | 2021-08-18 | Preparation method of o-nitrobenzenesulfonyl chloride |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4632693A (en) * | 1984-05-24 | 1986-12-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CN1150796A (en) * | 1995-04-17 | 1997-05-28 | 住友精化株式会社 | Process for preparation of aromatic or heteroaromatic sulfonyl halides |
| CN106831502A (en) * | 2017-03-13 | 2017-06-13 | 苏州市泽宸贸易有限公司 | Ortho-nitrophenyl sulfonic acid chloride, its synthetic method and application |
| CN108238986A (en) * | 2017-08-19 | 2018-07-03 | 成都千叶龙华石油工程技术咨询有限公司 | The synthetic method of pharmaceutical intermediate ortho-nitrophenyl sulfonic acid chloride |
| CN110105251A (en) * | 2019-05-20 | 2019-08-09 | 苏州市泽宸贸易有限公司 | A kind of industrialized preparing process of ortho-nitrophenyl sulfonic acid chloride |
-
2021
- 2021-08-18 CN CN202110947162.6A patent/CN113666848A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4632693A (en) * | 1984-05-24 | 1986-12-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CN1150796A (en) * | 1995-04-17 | 1997-05-28 | 住友精化株式会社 | Process for preparation of aromatic or heteroaromatic sulfonyl halides |
| CN106831502A (en) * | 2017-03-13 | 2017-06-13 | 苏州市泽宸贸易有限公司 | Ortho-nitrophenyl sulfonic acid chloride, its synthetic method and application |
| CN108238986A (en) * | 2017-08-19 | 2018-07-03 | 成都千叶龙华石油工程技术咨询有限公司 | The synthetic method of pharmaceutical intermediate ortho-nitrophenyl sulfonic acid chloride |
| CN110105251A (en) * | 2019-05-20 | 2019-08-09 | 苏州市泽宸贸易有限公司 | A kind of industrialized preparing process of ortho-nitrophenyl sulfonic acid chloride |
Non-Patent Citations (2)
| Title |
|---|
| BAO-LEI WANG等: "Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 117, pages 167 - 178, XP029532809, DOI: 10.1016/j.ejmech.2016.04.005 * |
| 陈旭东等: "2-氨基-N-甲基-N-环己基苯磺酰胺的合成研究", 染料工业, vol. 36, no. 4, pages 26 - 29 * |
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Application publication date: 20211119 |