CN116947712A - Synthesis method of sulfonamide organic compound - Google Patents

Synthesis method of sulfonamide organic compound Download PDF

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CN116947712A
CN116947712A CN202310918157.1A CN202310918157A CN116947712A CN 116947712 A CN116947712 A CN 116947712A CN 202310918157 A CN202310918157 A CN 202310918157A CN 116947712 A CN116947712 A CN 116947712A
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reaction
sulfonamide
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刘辉
陆军
刘明荣
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Suzhou Huadao Biological Pharmacy Co ltd
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Suzhou Huadao Biological Pharmacy Co ltd
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    • 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
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The application discloses a synthesis method of sulfonamide organic compounds, which takes sulfonyl chloride derivatives and primary amine or secondary amine as raw materials, and carries out heating reaction in a reaction solvent to obtain sulfonamide organic compounds with corresponding structures. According to the synthesis method of the sulfonamide organic compound, sulfonyl chloride derivatives represented by the structural formula (1) and primary amine or secondary amine are used as raw materials, through the design of a reaction solvent and heating temperature, hydrogen chloride generated by the reaction can firstly form ammonium salt with the primary amine or the secondary amine, then volatilize and escape, and the hydrogen chloride gas generated by the reaction can be effectively removed without adding an acid binding agent, so that the purposes of simplifying operation, saving cost and reducing micro waste yield are realized.

Description

Synthesis method of sulfonamide organic compound
Technical Field
The application relates to the technical field of organic chemical synthesis, in particular to a synthesis method of sulfonamide organic compounds.
Background
Sulfonamide organic compounds are extremely important chemical products and are widely applied to various fields.
For example, in hydrometallurgy and wastewater treatment, a metal extractant is required to extract and enrich related metal ions in water, and sulfonamide organic compounds are used as metal chelating agents, so that the metal chelating agents have extremely strong chelation effects on divalent metal ions such as copper (II), zinc (II), nickel (II), cobalt (II), cadmium (II), mercury (II), lead (II), iron (II) and the like, can selectively chelate and precipitate the divalent metal ions, and achieve the purpose of removing the metal ions from an aqueous solution. Among these, the relatively excellent sulfonamide metal chelators are 2- (dodecylbenzenesulfonamide) thiazole and 2- (dodecylbenzenesulfonamide) benzothiazole.
Another important application of sulfonamide organic compounds is as plasticizers, widely used in the production of engineering plastics and nylon. They act as plasticizers which weaken the adhesion between polymer molecules, reduce the frictional resistance of the molecular chains to each other, thus playing a role in lubrication, showing an improvement in flowability in a macroscopic sense, improving the processability of the polymer and the flexibility of the product, and enhancing the expansibility, impact resistance and abrasion resistance of the product. Among the more desirable sulfonamide plasticizers are N-butylbenzenesulfonamide, N-cyclohexyltosylamide, N' -p-cyclohexyl-bisbenzenesulfonamide, and the like.
In addition, sulfonamide-based organic compounds can also be used as functional materials in dental restorative materials, such as N-ethyltoluene sulfonamide.
Although sulfonamide organic compounds have different roles as a class of functional materials and have been used in various fields, the synthesis methods are basically consistent. In the prior art, sulfonyl chloride and amine with different structures are mostly adopted, and hydrogen chloride acidic gas generated in the reaction process is removed under the action of organic alkali such as triethylamine and pyridine or inorganic alkali such as sodium hydroxide, potassium hydroxide and carbonate serving as an acid binding agent. For example, chinese patent CN 101781244B discloses a preparation method of a compound 4-bromo-N- (pyridine-2-methyl) naphthalene-1-sulfonamide, which is prepared by using triethylamine as an acid binding agent.
However, in the process of realizing the technical scheme in the embodiment of the application, the inventor discovers that the existing preparation method of the sulfonamide compound at least has the following technical problems:
most of the methods can generate a large amount of hazardous wastes such as waste water, waste salt and the like, have the defects of serious environmental pollution, high production cost and the like, and do not meet the requirements of green and environment-friendly production.
Disclosure of Invention
The application solves the problems existing in the synthesis of sulfonamide organic compounds in the prior art by providing a synthesis method of sulfonamide organic compounds.
In order to solve the technical problems, the application provides a synthesis method of sulfonamide organic compounds, which takes a compound with a structural formula (1) and primary amine or secondary amine as raw materials, and carries out heating reaction in a reaction solvent to obtain sulfonamide organic compounds with corresponding structures;
wherein R is phenyl; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; phenyl substituted by fluorine, chlorine, bromine, carboxyl, amino or nitro; a halogenated hydrocarbon group; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; c containing sulfur, oxygen, nitrogen hetero atoms substituted by halogen, carboxyl, amino or nitro groups 3 -C 6 A heterocyclic group; aryl substituted by halogen, carboxyl, amino or nitro and containing sulfur, oxygen or nitrogen hetero atoms C 3 -C 6 A heterocyclic group.
In a preferred embodiment of the present application, the ratio of the amount of the compound of formula (1) to the amount of the primary amine or secondary amine is 1:1 to 1.2.
In a preferred embodiment of the application, the heating temperature is 80-140 ℃.
In a preferred embodiment of the application, the heating temperature is 100-120 ℃.
In a preferred embodiment of the present application, the reaction solvent comprises at least one of water, methanol, ethanol, isopropanol, N-butanol, cyclohexanol, ethylene glycol dimethyl ether, benzene, toluene, xylene, acetonitrile, acetone, 2-butanone, N-dimethylformamide, dimethyl sulfoxide, sulfolane, ethyl acetate, butyl acetate, petroleum ether, decalin, tetrahydronaphthalene, tetrahydrofuran, methyltetrahydrofuran, or 1, 4-dioxane.
In a preferred embodiment of the present application, the reaction solvent includes at least one of ethylene glycol dimethyl ether, toluene, xylene, dimethyl sulfoxide, butyl acetate, or 1, 4-dioxane.
The beneficial effects of the application are as follows: according to the synthesis method of the sulfonamide organic compound, sulfonyl chloride derivatives represented by the structural formula (1) and primary amine or secondary amine are used as raw materials, through the design of a reaction solvent and heating temperature, hydrogen chloride generated by the reaction can firstly form ammonium salt with the primary amine or the secondary amine, then volatilize and escape, and the hydrogen chloride gas generated by the reaction can be effectively removed without adding an acid binding agent, so that the purposes of simplifying operation, saving cost and reducing micro waste yield are realized.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of 4- (5-bromopyridine-3-ylsulfonyl) morpholine prepared in example 5 of the present application.
Detailed Description
The preferred embodiments of the present application will be described in detail below with reference to the accompanying drawings so that the advantages and features of the present application can be more easily understood by those skilled in the art, thereby making clear and defining the scope of the present application.
Referring to fig. 1, an embodiment of the present application includes:
the sulfonyl chloride derivative is represented by a structural formula (1), and concretely comprises the following components:
wherein R is phenyl; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; phenyl substituted by fluorine, chlorine, bromine, carboxyl, amino or nitro; a halogenated hydrocarbon group; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; c containing sulfur, oxygen, nitrogen hetero atoms substituted by halogen, carboxyl, amino or nitro groups 3 -C 6 A heterocyclic group; aryl substituted by halogen, carboxyl, amino or nitro and containing sulfur, oxygen or nitrogen hetero atoms C 3 -C 6 A heterocyclic group.
Dropwise adding sulfonyl chloride derivatives represented by the structural formula (1) into a reaction solvent added with primary amine or secondary amine, controlling the mass ratio of the dropwise added sulfonyl chloride derivatives to the primary amine or secondary amine to be 1:1-1.2, then carrying out heating reaction until the sulfonyl chloride derivatives are completely reacted by gas phase detection, and then obtaining the target product sulfonamide organic compound.
Wherein the heating temperature is 80-140 ℃, preferably 100-120 ℃. The temperature condition is favorable for the decomposition of ammonium salt and the volatilization of decomposed hydrogen chloride gas.
The reaction solvent is at least one of the following substances: water, methanol, ethanol, isopropanol, N-butanol, cyclohexanol, ethylene glycol dimethyl ether, benzene, toluene, xylene, acetonitrile, acetone, 2-butanone, N-dimethylformamide, dimethyl sulfoxide, sulfolane, ethyl acetate, butyl acetate, petroleum ether, decalin, tetrahydronaphthalene, tetrahydrofuran, methyltetrahydrofuran, or 1, 4-dioxane. Preferably ethylene glycol dimethyl ether, toluene, xylene, dimethyl sulfoxide, butyl acetate or 1, 4-dioxane. The reaction solvent does not react with hydrogen chloride gas, and hydrogen chloride gas is not stored, so that the decomposed hydrogen chloride gas is easy to volatilize in time from the reaction solvent under the heating condition.
In the reaction process, sulfonyl chloride derivatives represented by the structural formula (1) are dropwise added into a reaction system to react with primary amine or secondary amine to generate hydrogen chloride, the hydrogen chloride reacts with the primary amine or the secondary amine to form ammonium salt, the generated ammonium salt is decomposed again under the heating condition, decomposed hydrogen chloride gas volatilizes from a reaction solvent under the heating condition, and the decomposed free primary amine or secondary amine continuously reacts with sulfonyl chloride derivatives represented by the structural formula (1) to obtain the sulfonamide organic compound. Therefore, the whole reaction process can be completed without adding an acid binding agent through the selection of raw materials, reaction temperature and reaction solvent, and a target product is obtained, so that the purposes of saving raw materials, simplifying the reaction process, reducing production cost and reducing micro waste are achieved, and the method is environment-friendly.
Example 1
Synthesis of N-butylbenzenesulfonamide
Adding 44 kg of N-butylamine and 100 liters of toluene into a 1000 liter reaction kettle, then dropwise adding 100 kg of benzenesulfonyl chloride and 10 liters of N, N-dimethylformamide solution into the overhead tank, and controlling the temperature of a reaction system in the reaction kettle to be not more than 50 ℃; after the completion of the dropwise addition, stirring for 30 minutes, heating to 110 ℃ for reaction for 2 hours, and detecting that the benzenesulfonyl chloride is reacted completely in a gas phase.
The toluene solvent is recovered by distillation, the bottom material is transferred into a reduced pressure distillation kettle, all low boiling point substances are removed by reduced pressure distillation through a water flushing pump, then the distillation kettle is switched into a high vacuum decompression system for reduced pressure distillation purification, and the fractions with the speed of 150-160 ℃/0.1mmHg are collected to obtain 118 kg of products, the yield is 98 percent, 1HNMR (400 MHz, CDCl 3): 0.84 (t, J=8.1 Hz, 3H), 1.22-1.33 (m, 2H), 1.39-1.45 (m, 2H), 2.95 (q, J=8.1 Hz, 2H), 5.01 (brs, 1H), 7.48-7.59 (m, 3H) and 7.88-7.89 (m, 2H).
Example 2
Synthesis of N-benzyl benzene sulfonamide
3.4 kg of benzylamine, 10 l of benzene and 1 l of water are put into a 30 l reaction kettle, and 5 kg of benzenesulfonyl chloride is quickly added dropwise under full stirring; after the dripping is finished, heating to 115 ℃ to react for 3 hours, and detecting the benzenesulfonyl chloride in a gas phase to finish the reaction; stopping heating, standing for layering, and removing the lower water phase by separating liquid; about half of the solvent was removed by distillation with heating, cooling to-5℃with stirring for crystallization for 2 hours, suction filtration, washing with 1mol/L hydrochloric acid once, and drying to give 6.7 kg of the product in 96% yield, 1HNMR (400 MHz, d 6-DMSO): 4.01 (d, t=2.6 Hz, 2H), 7.25-7.32 (m, 5H), 7.59-7.68 (m, 3H), 7.84-7.52 (m, 2H), 7.95 (s, 1H).
Example 3
Synthesis of N-tert-butyl-4-fluorobenzenesulfonamide
5 kg of 4-fluorobenzenesulfonyl chloride and 10 l of ethylene glycol dimethyl ether are put into a 30 l reaction kettle, and 2 kg of tert-butylamine and 2 l of aqueous solution are rapidly and dropwise added under the condition of full stirring and temperature control below 60 ℃; after the dripping is finished, heating to 100 ℃ to react for 2 hours, and detecting the benzene sulfonyl chloride in a gas phase to finish the reaction; stopping heating, adding 10L of water, starting circulating cooling, cooling to 0 ℃, stirring and crystallizing for 2 hours, filtering, washing once with 1mol/L hydrochloric acid, washing with water, and drying to obtain 5.2 kg of product with the yield of 95%, wherein 1HNMR (400 MHz, CDCl 3): 1.23 (s, 9H), 4.82 (s, 1H), 7.14-7.27 (m, 2H) and 7.91-7.93 (m, 2H).
Example 4
Synthesis of N- (2-hydroxyethyl) p-toluenesulfonamide
Adding 0.38 kg of ethanolamine and 4 liters of water into a 10 liter reaction kettle, and dropwise adding 1 kg of p-toluenesulfonyl chloride and 5 liters of butyl acetate solution in 1 hour under full stirring; after the dripping is finished, heating to 100 ℃ to react for 2 hours, and detecting that the p-toluenesulfonyl chloride is reacted in a gas phase; stopping heating, adding 2L of water, fully stirring, standing for layering, separating to remove a lower water phase, drying an organic phase by using anhydrous sodium sulfate, filtering, concentrating the filtrate to one third, slowly adding 2L of petroleum ether under cooling of ice salt, stirring for crystallization, filtering, and drying to obtain 1.03 kg of a product, wherein the yield is 98%,1HNMR (400 MHz, CDCl 3): 2.44 (s, 3H), 3.08 (t, J=4 Hz, 2H), 3.69 (t, J=4 Hz, 2H), 5.74 (s, 1H), 7.33 (d, J=8 Hz, 2H), 7.78 (d, J=8 Hz, 2H).
Example 5
Synthesis of 4- (5-bromopyridine-3-ylsulfonyl) morpholine
5 g of 5-bromo-pyridine-3-sulfonyl chloride and 50 ml of 1, 4-dioxane are added into a reaction bottle, 1.9 g of morpholine is added after stirring and dissolution, and the mixture is heated to 105 ℃ for reaction for 4 hours; the reaction was completely checked by gas phase, cooled, 25 g of silica gel was added, concentrated to dryness and the residue was purified by flash column chromatography with petroleum ether ethyl acetate=5:1 (v/v) as eluent to give 5.9 g of the product in 98% yield, 1HNMR (400 mhz, d 6-DMSO): 3.00 (t, j=4.6 hz,4 h), 3.65 (t, j=4.6 hz,4 h), 8.40 (t, j=2.2 hz,1 h), 8.90 (d, j=2 hz,1 h), 9.08 (d, j=2.4 hz,1 h).
Example 6
Synthesis of N-tert-butyl-3-nitrobenzenesulfonamide
5 kg of 3-nitrobenzenesulfonyl chloride, 10 l of dimethylbenzene and 1 l of dimethyl sulfoxide are put into a 30-liter reaction kettle, and 2 kg of tert-butylamine is rapidly added dropwise under sufficient stirring; after the dripping is finished, heating to 110 ℃ to react for 5 hours, and detecting the 3-nitrobenzenesulfonyl chloride in a gas phase to finish the reaction; stopping heating, starting circulating cooling, cooling to-5 ℃ and stirring for crystallization for 2 hours, filtering, washing with xylene twice, and drying to obtain 5.7 kg of products, wherein the yield is 98%,1HNMR (400 MHz, CDCl 3): 1.27 (s, 9H), 4.83 (brs, 1H), 7.73 (t, J=8 Hz, 1H), 8.20-8.24 (m, 1H), 8.39-8.42 (m, 1H), 8.75 (t, J=2.2 Hz, 1H).
Example 7
Synthesis of N- (3-bromophenyl) benzenesulfonamide
100 kg of 3-bromoaniline and 200 l of butyl acetate are put into a 500 l reaction kettle, and 98 kg of benzenesulfonyl chloride is rapidly added dropwise under the condition of full stirring and temperature control below 60 ℃; after the dripping is finished, heating to 115 ℃ to react for 5 hours, and detecting the benzenesulfonyl chloride in a gas phase to finish the reaction; about half of the solvent was distilled off under reduced pressure, heating was stopped, circulation cooling was started, cooling to-8℃and stirring crystallization was carried out for 5 hours, suction filtration was carried out, butyl acetate washing was carried out twice, and 169 kg of the product was obtained by drying, and the yield was 98%,1HNMR (400 MHz, d 6-DMSO): 7.10-7.12 (m, 1H), 7.19-7.24 (m, 3H), 7.56-7.76 (m, 3H), 7.76-7.79 (m, 2H), 10.59 (s, 1H).
Example 8
Synthesis of N-tert-butyl-3-chloropropane-1-sulfonamide
25 kg of 3-chloropropionyl chloride and 50 l of tetrahydrofuran are put into a 100 l reaction kettle, and 11.5 kg of tert-butylamine is rapidly added dropwise under the condition of full stirring and temperature control below 60 ℃; after the dripping is finished, heating to 100 ℃ to react for 6 hours, and detecting that the 3-chloropropionyl chloride is completely reacted in a gas phase; the solvent was distilled off under reduced pressure, the heating was stopped, 50L of 2mol/L hydrochloric acid was added, the circulation cooling was started, the cooling was carried out to 0℃and the stirring crystallization was carried out for 2 hours, the filtration was carried out, the washing was carried out once with 1mol/L hydrochloric acid, the washing was carried out with water, and the drying was carried out to obtain 28.7 kg of the product, the yield was 95%,1HNMR (400 MHz, CDCl 3): 1.34 (s, 9H), 2.20-2.29 (m, 2H), 3.18 (t, J=10 Hz, 2H), 3.65 (t, J=10 Hz, 2H) and 4.43 (s, 1H).
Example 9
Synthesis of N, N-dimethyl-4-bromobenzenesulfonamide
4 kg of 4-bromobenzenesulfonyl chloride and 10 l of 1, 4-dioxane are put into a 30 l reaction kettle, the solution is fully stirred and cleared, and 2.1 kg of 40% dimethylamine water solution is quickly dripped below the temperature of 60 ℃; after the dripping is finished, heating to 100 ℃ to react for 3 hours, and detecting the reaction of the 4-bromobenzenesulfonyl chloride in a gas phase; stopping heating, adding 10L of water, starting circulating cooling, cooling to-5 ℃, stirring and crystallizing for 2 hours, filtering, washing once with 1mol/L hydrochloric acid, washing with water, and drying to obtain 3.96 kg of products, wherein the yield is 96%,1HNMR (400 MHz, CDCl 3): 2.72 (s, 6H), 7.64 (d, J=8 Hz, 2H) and 7.69 (d, J=12 Hz, 2H).
The foregoing description is only illustrative of the present application and is not intended to limit the scope of the application, and all equivalent structures or equivalent processes or direct or indirect application in other related technical fields are included in the scope of the present application.

Claims (6)

1. A synthesis method of sulfonamide organic compounds is characterized in that a compound with a structural formula (1) and primary amine or secondary amine are used as raw materials, and heating reaction is carried out in a reaction solvent to obtain sulfonamide organic compounds with corresponding structures;
wherein R is phenyl; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; phenyl substituted by fluorine, chlorine, bromine, carboxyl, amino or nitro; a halogenated hydrocarbon group; c containing sulfur, oxygen, nitrogen hetero atoms 3 -C 6 A heterocyclic group; c containing sulfur, oxygen, nitrogen hetero atoms substituted by halogen, carboxyl, amino or nitro groups 3 -C 6 A heterocyclic group; aryl substituted by halogen, carboxyl, amino or nitro and containing sulfur, oxygen or nitrogen hetero atoms C 3 -C 6 A heterocyclic group.
2. The method for synthesizing a sulfonamide compound according to claim 1, wherein the ratio of the amount of the compound of formula (1) to the amount of the substance of the primary amine or the secondary amine is 1:1 to 1.2.
3. The method for synthesizing a sulfonamide compound according to claim 1, wherein the heating temperature is 80 to 140 ℃.
4. The method for synthesizing a sulfonamide compound according to claim 2, wherein the heating temperature is 100 to 120 ℃.
5. The method for synthesizing a sulfonamide compound according to claim 1, wherein the reaction solvent comprises at least one of water, methanol, ethanol, isopropanol, N-butanol, cyclohexanol, ethylene glycol dimethyl ether, benzene, toluene, xylene, acetonitrile, acetone, 2-butanone, N-dimethylformamide, dimethyl sulfoxide, sulfolane, ethyl acetate, butyl acetate, petroleum ether, decalin, tetrahydronaphthalene, tetrahydrofuran, methyltetrahydrofuran, or 1, 4-dioxane.
6. The method for synthesizing a sulfonamide compound according to claim 5, wherein the reaction solvent comprises at least one of ethylene glycol dimethyl ether, toluene, xylene, dimethyl sulfoxide, butyl acetate, and 1, 4-dioxane.
CN202310918157.1A 2023-07-25 2023-07-25 Synthesis method of sulfonamide organic compound Pending CN116947712A (en)

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