CN117736139A - Synthesis method of pyridine-3-sulfonyl chloride - Google Patents
Synthesis method of pyridine-3-sulfonyl chloride Download PDFInfo
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- CN117736139A CN117736139A CN202211114173.7A CN202211114173A CN117736139A CN 117736139 A CN117736139 A CN 117736139A CN 202211114173 A CN202211114173 A CN 202211114173A CN 117736139 A CN117736139 A CN 117736139A
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- Prior art keywords
- pyridine
- chloride
- sulfonyl chloride
- compound
- diazonium salt
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- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title claims description 4
- 239000012954 diazonium Substances 0.000 claims abstract description 30
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 23
- -1 zinc chloride diazonium salt Chemical class 0.000 claims abstract description 22
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 17
- 239000011592 zinc chloride Substances 0.000 claims abstract description 17
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000007858 starting material Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 9
- 238000006193 diazotization reaction Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 239000003929 acidic solution Substances 0.000 claims 1
- 229960003280 cupric chloride Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000002699 waste material Substances 0.000 abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- ROGSHYHKHPCCJW-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-n-methylmethanamine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CN=CC=1S(=O)(=O)N1C=C(CNC)C=C1C1=CC=CC=C1F ROGSHYHKHPCCJW-WLHGVMLRSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229950003825 vonoprazan Drugs 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
The invention provides a synthetic method for synthesizing pyridine-3-sulfonyl chloride. The synthesis of pyridine-3-sulfonyl chloride takes 3-aminopyridine as a starting material, and the separated intermediate zinc chloride diazonium salt is subjected to sulfonyl chlorination reaction. The method has the advantages of low cost, high product content, convenient operation and less three wastes, and is suitable for industrialized amplified production.
Description
Technical field:
the invention relates to the field of pharmaceutical chemistry, in particular to a novel synthesis method of pyridine-3-sulfonyl chloride.
The background technology is as follows:
the pyridine-3-sulfonyl chloride has the structural formula:
pyridine-3-sulfonyl chloride is an important pharmaceutical intermediate, which is widely used in the synthesis of drugs, and is mainly used for preparing TAK-438.
Regarding the synthesis of pyridine-3-sulfonyl chloride, it is currently synthesized mainly by the following route:
route one: reference may be made to the method of CN 201810991672.1:
the method has the advantages that the cost is low due to the use of sodium hydrosulfide or potassium hydrosulfide and the like, but in the industrial production process, the smell of the sulfhydryl compound is heavy, the chlorine needs to be introduced in the second step, the safety risk is high, and the factors are not beneficial to industrial production.
Route two: journal of the American Chemical Society,1992, vol.114, #12, p.4889-4898
In the first step of the route, sulfuric acid or chlorosulfonic acid is used for generating pyridine-3-sulfonic acid, and in the second step, phosphorus trichloride and the like are used for chlorination. When pyridine-3-sulfonic acid is generated in the first step, a small amount of pyridine-3-sulfonic acid is positioned at the 2 position or the 4 position, so that the pyridine-3-sulfonic acid is not easy to separate; and the pollution is large, a lot of waste acid water is generated, and the safety risk is also large when dangerous chemicals such as concentrated sulfuric acid or phosphorus oxychloride are used.
Route three: organic Process Research and Development,2009, vol.13, #5, p.875-879; CN106432067, etc
The method is characterized in that diazotization reaction is carried out, chlorinated heavy chloride salt generated in the middle is unstable, side reactions are more, and the pyridine-3-sulfonyl chloride product is colorless liquid, but the sulfonyl chloride product can be deteriorated when distilled at high temperature, so that the purity requirement on the reaction process is higher, that is, side reactions cannot be carried out when the reaction occurs, and obviously, the route cannot meet the requirement.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, and provides a preparation method of pyridine-3-sulfonyl chloride with high yield and environmental protection, which is mainly an improvement on a diazotization route, and the specific reaction equation is as follows:
the synthesis scheme comprises the following preferable steps:
the first step (preparation of ferric chloride diazonium salt or zinc chloride diazonium salt):
adding 3-aminopyridine into dilute hydrochloric acid, cooling to-5-0 ℃, dropwise adding sodium nitrite aqueous solution, controlling the temperature below 0 ℃, then dropwise adding 30% zinc chloride aqueous solution, controlling the temperature to 0-5 ℃, filtering, washing a filter cake once with dilute acid, washing once with a small amount of methanol, and drying. Thus obtaining zinc chloride diazonium salt.
And a second step of:
dropwise adding thionyl chloride into water, then cooling to about 0 ℃, adding cuprous chloride after dropwise adding, cooling to-5 ℃, adding zinc chloride diazonium salt prepared in the previous step into the solution in batches, controlling the temperature to be 0-5 ℃, then reacting overnight at the same temperature, extracting with ethyl acetate for 2 times after the reaction is finished, washing with saturated sodium bicarbonate aqueous solution for 1 time, washing with water for one time, and finally washing with saturated salt for 1 time. Concentrating the ethyl acetate, stirring, cooling to-5 ℃, crystallizing, filtering, and drying. Obtaining pure pyridine-3-sulfonyl chloride.
Wherein the mole ratio of the 3-aminopyridine, sodium nitrite, zinc chloride aqueous solution and dilute hydrochloric acid in the first step is 1 (1.0-1.1): 1.0-1.2): 3-4; the molar ratio of the zinc chloride diazonium salt, the sulfoxide chloride and the cuprous chloride in the second step is 1 (2-2.2) (0.005-0.01), wherein the reaction temperature in the first step and the second step is controlled at 0-5 ℃.
Compared with the prior art, the invention has the advantages that:
1. the traditional diazonium salt is unstable and can be slowly decomposed even at the temperature of minus 5 ℃ so as to generate side reaction, thereby increasing the post-treatment difficulty; the Lewis acid diazonium salt is quite stable, does not have any danger, can prepare the pure fluoboric acid diazonium salt without decomposition even under the room temperature condition
2. Meanwhile, due to higher stability, pure products can be separated out, and then when the product is put into the next reaction, the side reaction is reduced greatly compared with the traditional diazonium salt, and the yield is improved correspondingly. The total yield of the traditional hydrochloric acid diazotization or dilute sulfuric acid diazotization reaction is generally 40-60%, and the yield of the Lewis acid diazotization reaction can reach 70-90%.
3. After separating out diazonium salt, the reaction liquid of preparing Lewis acid diazonium salt may be further thrown into the next batch to reduce acid waste water. Because of high stability, even if a small amount of Lewis acid diazonium salt still exists in the reaction liquid, the next batch of reaction is not influenced; the diazonium salt prepared by the prior art is usually dissolved in water, and can only be put into the next reaction by using an aqueous solution of the diazonium salt.
4. Because the diazotization reaction is an exothermic reaction, the heat exchange efficiency and the temperature control of the traditional diazonium salt on the reaction kettle are very high, namely the reaction time and the temperature are required at the same time, the reaction time for preparing the diazonium salt is not suitable for more than 4 hours, the temperature is different according to different reaction substrates, and the temperature for preparing the diazonium salt is usually controlled below-5 ℃, namely the temperature is required to be ensured to be not more than-5 ℃ and the time is required to be ensured to be not more than 4 hours, so that the heat exchange efficiency of the reaction kettle is very high. The preparation condition of the Lewis acid diazonium salt is mild, and the 3-aminopyridine is taken as an example, so that the reaction temperature can be controlled below 10 ℃ generally, side reactions can not occur, the requirements on a refrigerator are not high, the temperature controllable range is much larger, and the reaction time can be prolonged to 6-8 hours and can not be decomposed.
5. Among the Lewis acid diazonium salts, only the fluoroboric acid diazonium salt, the zinc chloride diazonium salt, the ferric chloride diazonium salt, etc. are available at present in consideration of the operability, the yield, the byproducts, the three wastes, etc., and the zinc chloride diazonium salt has lower cost than the ferric chloride diazonium salt and the fluoroboric acid diazonium salt, and the same effect can be obtained.
Drawings
In the drawings of the specification: FIG. 1 is an HPLC profile of compound C (i.e., pyridine-3-sulfonyl chloride) and related data.
FIG. 2 is a synthetic route diagram for pyridine-3-sulfonyl chloride.
Detailed Description
The invention is further described with reference to the following detailed drawings, in order to make the technical means, authoring features, workflow, and usage method of the invention achieve the purpose and efficacy easily understood.
Synthesis of Compound B:
94 g (1 mol) of 3-aminopyridine and 670ml of 6mol/L dilute hydrochloric acid are added into a reaction bottle, cooled to 0-5 ℃, then an aqueous solution of sodium nitrite (72.45g+150 ml of water) is added dropwise, the temperature is controlled to 0-5 ℃, then an aqueous solution of zinc chloride (136.4 g, 300 ml) is added dropwise, the temperature is controlled to 0-5 ℃, the mixture is stirred for 30-60 minutes at 0-5 ℃ after the dripping is finished, suction filtration is carried out, a filter cake is leached for 1 time by 100ml of 6mol/L dilute hydrochloric acid (0-5 ℃) of ice, and the compound B180.9g is obtained after drying, and the yield is 95.3%.
Synthesis of Compound C:
238 g (2 mol) of thionyl chloride is added dropwise to 500ml of water, then cooled to about 0-5 ℃, 1g (0.01 mol) of cuprous chloride is added after the dropwise addition, zinc chloride diazonium salt prepared in the first step is added into the solution in batches, the temperature is controlled between 0 and 5 ℃, then the reaction is carried out overnight at 0 to 5 ℃, after the reaction is finished, dichloromethane (300 ml is used for 2 times) is used for extraction, the organic layers are combined, the organic layers are washed with 300ml of saturated sodium bicarbonate aqueous solution for 1 time, then 300ml of water is used for one time, finally 300ml of saturated salt water is used for 1 time, then anhydrous sodium sulfate is used for drying, suction filtration is carried out, and the filtrate is concentrated to remove the dichloromethane, thus 161.0g of compound C, namely pyridine-3-sulfonyl chloride, and the yield is 90.7%. The HPLC detection spectrogram is shown in figure 1 in the drawings of the specification. Nuclear magnetic data: 1 H NMR(400MHz，CDCl 3 ),δ:7.70-7.74(dd，1H),8.43-8.45(dd,1H),9.03-9.05(dd,1H),9.31-9.32(d,1H).
the foregoing has shown and described the basic principles and main features of the present invention and the advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (7)
1. The synthesis method of pyridine-3-sulfonyl chloride is characterized in that the pyridine-3-sulfonyl chloride is prepared by taking 3-aminopyridine as a starting material and performing zinc chloride diazotization reaction:
the first step is that the compound A reacts with sodium nitrite aqueous solution and zinc chloride aqueous solution in acid solution to generate zinc chloride diazonium salt with a compound B structure. . The second step is that the compound B and thionyl chloride are reacted under the condition of catalyst to generate the compound C.
2. The method for preparing pyridine-3-sulfonyl chloride according to claim 1, wherein the acidic solution is diluted hydrochloric acid of 6 to 10 mol/L.
3. The method for preparing pyridine-3-sulfonyl chloride according to claim 1, wherein the molar ratio of the aqueous solution of sodium nitrite to the aqueous solution of zinc chloride to the compound a is 1.0 to 1.1:1.0 to 1.2:1.
4. The method for producing pyridine-3-sulfonyl chloride according to claim 1, wherein the diazotization reaction is carried out at a reaction temperature of 5 ℃ or less.
5. The method for preparing pyridine-3-sulfonyl chloride according to claim 1, wherein the compound B, namely zinc chloride diazonium salt, is subjected to acyl chlorination reaction to obtain the compound C, namely pyridine-3-sulfonyl chloride.
6. The method for preparing pyridine-3-sulfonyl chloride according to claim 1, wherein the zinc chloride diazonium salt with the structure of formula II and the thionyl chloride solution containing the catalyst undergo the acyl chlorination reaction to form the compound C, pyridine-3-sulfonyl chloride.
7. The method for preparing pyridine-3-sulfonyl chloride according to claim 1, wherein the catalyst is cuprous chloride or cupric chloride.
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| CN202211114173.7A CN117736139A (en) | 2022-09-14 | 2022-09-14 | Synthesis method of pyridine-3-sulfonyl chloride |
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| CN202211114173.7A CN117736139A (en) | 2022-09-14 | 2022-09-14 | Synthesis method of pyridine-3-sulfonyl chloride |
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| CN117736139A true CN117736139A (en) | 2024-03-22 |
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