CN102898340A - Synthesis method of S-substituted-anthranilate thioester derivatives - Google Patents
Synthesis method of S-substituted-anthranilate thioester derivatives Download PDFInfo
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Abstract
The invention discloses a synthesis method of S-substituted-anthranilate thioester derivatives disclosed as Formula (I), which comprises the following steps: sufficiently reacting isatoic anhydride compounds disclosed as Formula (II) and dithioether compounds disclosed as Formula (III) in an inert organic solvent at 0-120 DEG C in the presence of an accelerator and basic compounds; and after the reaction finishes, separating and purifying the reaction solution to obtain the S-substituted-anthranilate thioester derivatives disclosed as Formula (I). The method disclosed by the invention has the advantages of reasonable technological conditions, simple and safe operation, mild reaction conditions, high reaction yield, cheap and accessible raw materials, environment-friendly substrate, low production cost and fewer three wastes.
Description
(1) technical field
The present invention relates to the chemical synthesis process that a kind of S-replaces the anthranilic acid thioes derivatives.
(2) background technology
Thioes derivatives is the natural compounds with multifunctional usage, because its special structure can cause some compound to have pharmacologically active, it also is widely applied to the aspects such as medicine, agricultural chemicals by people.Simultaneously, thioes derivatives also is the important intermediate of a class in organic synthesis.Therefore, synthesizing in organic synthesis of thioes derivatives has great importance.Yet the preparation method of S-replacement anthranilic acid sulfur ester only has two examples (such as J. Org. Chem. 1959,24,1214 and Tetrahedron Lett. 2010,51,5368) as far as we know.These reports all synthesize S-with the reaction of isatoic anhydride and thiophenol and replace the anthranilic acid sulfur ester.Yet the method has adopted that toxicity is large, volatility is large and what have foul smell is raw material to methylbenzene phenyl-sulfhydrate, and to having relatively high expectations of equipment, and danger coefficient is large in the production process.Therefore, the popularization of these methods mentioned above is restricted.
For the above unfavorable factor of considering, be necessary existing technique is improved, develop a kind of synthetic method with advantages such as reaction conditions gentleness, efficient, production cost is low, for the synthetic new technology that provides of anthranilic acid sulfur ester is provided S-.
(3) summary of the invention
The purpose of this invention is to provide a kind of technique rationally, hypotoxicity, reaction conditions is gentle, reaction yield is high and the S-of good product quality replaces the chemical synthesis process of anthranilic acid thioes derivatives.
For achieving the above object, the present invention adopts following technical scheme:
A kind of S-as shown in the formula (I) replaces the synthetic method of anthranilic acid thioes derivatives, described method is: isatoic anhydride compounds as shown in the formula (II) and disulfide compound as shown in the formula (III) are raw material, in the presence of promotor and basic cpd, in inert organic solvents, fully reaction under 0 ~ 120 ℃ temperature of reaction, TLC follows the tracks of detection to reacting completely, and reaction solution obtains described S-as shown in the formula (I) through separation and purification and replaces the anthranilic acid thioes derivatives;
In formula (I) or the formula (II), R
1Be selected from one of following: the alkoxyl group of the alkyl of hydrogen, C1～C8, the alkyloyl of C1～C8, C1～C8 is preferably hydrogen or methyl.
In formula (I) or the formula (II), the H on phenyl ring or the aromatic nucleus is not substituted or is substituted basic R
2Replace described substituent R
2Be selected from one of following: the alkyl of C1～C8, halogen, trifluoromethyl, nitro; H on preferred phenyl ring or the aromatic nucleus is not substituted or is substituted basic R
2Replace described substituent R
2Be preferably one of following: chlorine, methyl, nitro most preferably are chlorine or methyl; Most preferably the H on phenyl ring or the aromatic nucleus is not substituted.
In formula (I) or the formula (III), it is one of following that R is selected from: the alkyl of C2～C8, benzyl, phenyl, substituted-phenyl, and in the described substituted-phenyl, the substituting group on the phenyl ring is the alkyl of C1～C8, alkoxyl group, halogen or the trifluoromethyl of C1～C8; It is one of following that R is preferably: benzyl, phenyl, substituted-phenyl, in the described substituted-phenyl, the substituting group on the phenyl ring is preferably from one of following: methyl or chlorine
Halogen of the present invention is F, Cl, Br or I.
The reaction formula of described reaction is:
It is one of following that described promotor is selected from: S-WAT, sodium bisulfite, V-Brite B, rongalite, Sodium Pyrosulfite, Sulfothiorine; Be preferably V-Brite B or rongalite, most preferably be V-Brite B.
The ratio of the amount of substance of the disulfide compound shown in the described formula (III), isatoic anhydride compounds as shown in the formula (II), promotor, basic cpd is 1.0:1.0～4.0:1.0～6.0:2.5 ~ 4.5, be preferably 1.0:1.5～3.0:3.0～4.5:3 ~ 4, more preferably 1:2 ~ 2.5:3 ~ 4:3 ~ 4 most preferably are 1.0:2.5:4.0:3.0.
Among the present invention, the solvent of described inert organic solvents for not reacting with reactant, specifically can be selected from following one or more mixing: chlorobenzene, N, dinethylformamide, toluene, methyl-sulphoxide, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, ethyl acetate, N-Methyl pyrrolidone, tetracol phenixin, methylene dichloride, acetonitrile; Preferred described inert organic solvents is one of following: N-Methyl pyrrolidone, DMF, methyl-sulphoxide; Most preferably be methyl-sulphoxide.
The quality consumption of inert organic solvents of the present invention is 5～25 times of quality of disulfide compound as shown in the formula (III), is preferably 10～15 times.
Basic cpd of the present invention can be such as yellow soda ash, salt of wormwood, cesium carbonate, sodium bicarbonate, sodium-acetate, sodium hydroxide or potassium tert.-butoxide, is preferably salt of wormwood or cesium carbonate, more preferably salt of wormwood.
Described reaction solution through separation purification method is: after reaction finished, the water washing of reaction solution adding saturated common salt separated and gets organic layer, steamed after the drying to desolventize namely to get described S-replacement anthranilic acid thioes derivatives as shown in the formula (I).
Among the present invention, described temperature of reaction is 0 ~ 120 ℃, preferred 25 ~ 100 ℃, and most preferably 50 ~ 65 ℃.Reaction times is generally 0.5 ~ 10h, is preferably 1.5 ~ 3.5h.
Concrete, S-of the present invention replaces the synthetic method of anthranilic acid thioes derivatives to carry out in accordance with the following steps: as shown in the formula (II) isatoic anhydride compounds and promotor are dissolved in the inert organic solvents, stir and drip under 25 ~ 100 ℃ of temperature with the disulfide compound as shown in the formula (III) of same inert organic solvents dissolving and the solution of basic cpd, dropwise insulation reaction under rear 25 ~ 100 ℃ of temperature, the TLC tracking monitor is to reacting completely, reaction solution adds the saturated common salt water washing, separate and get organic layer, dry rear steaming desolventizes and namely gets described S-replacement anthranilic acid thioes derivatives as shown in the formula (I);
Described promotor is V-Brite B or rongalite;
The ratio of the amount of substance of the disulfide compound shown in the described formula (III), isatoic anhydride compounds as shown in the formula (II), promotor, basic cpd is 1.0:1.5～3.0:3.0～4.5:3 ~ 4;
Described inert organic solvents be following one or more mixing: DMF, methyl-sulphoxide, N-Methyl pyrrolidone.
The total quality consumption of described inert organic solvents is 5～25 times of quality of disulfide compound as shown in the formula (III).
Described inert organic solvents can be divided into two portions, a part is used for dissolving isatoic anhydride compounds and promotor as shown in the formula (II), remainder is used for dissolving disulfide compound and basic cpd as shown in the formula (III), 5～25 times of the quality that its total quality consumption is disulfide compound as shown in the formula (III).Be used for dissolving as shown in the formula (II) the isatoic anhydride compounds and the consumption of the part of promotor can be 30 ~ 70% of total consumption, be used for dissolving as shown in the formula (III) disulfide compound and the consumption of the part of basic cpd can be 30 ~ 70% of total consumption.These those skilled in the art can regulate solvent load voluntarily according to practical situation.
Described basic cpd is salt of wormwood or cesium carbonate.
The present invention compared with prior art, its beneficial effect is mainly reflected in: (1) processing condition are reasonable, safety simple to operate; (2) reaction conditions is gentle, and reaction yield is high; (3) used raw material is cheap and easy to get, and substrate is environmentally friendly, and production cost is low, and the three wastes are few; Therefore the present invention has larger implementary value and economic results in society.
(4) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 218g, and its total consumption is 10 times of Diphenyl disulfide ether quality.
Isatoic anhydride and promotor are dissolved in organic solvent (consumption of organic solvent is 6 times of Diphenyl disulfide ether quality).Diphenyl disulfide ether and salt of wormwood are dissolved in organic solvent (consumption of organic solvent is 4 times of Diphenyl disulfide ether quality), slowly drop in the solution of isatoic anhydride and promotor, temperature of reaction is 50 ℃, and afterreaction finished in 3.5 hours.
React complete after, add saturated aqueous common salt, extracting and separating is got organic layer.Rotation evaporate to dryness organic solvent and recovery namely get S-phenylanthranilic acid thioesters 18.8g, yield 82%, purity 97.8% after dry.
Nuclear magnetic resonance spectrum (Bruke):
1H NMR (500 MHz, CDCl
3) δ (ppm)=5.81 (s, 2H), 6.64-6.72 (m, 2H), 7.45-7.51 (m, 6H), 7.99-8.01 (m, 1H).
13C NMR (125 MHz, CDCl
3) δ (ppm)=116.3,117.1,117.5,127.9,129.1,129.4,130.2,134.6,135.6,148.5,191.3.
Embodiment 2:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is rongalite, the quality that feeds intake 61.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 218g, and its total consumption is 10 times of Diphenyl disulfide ether quality.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 14.2g, yield 62%, purity 97.5%.
Embodiment 3:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is N, N, and-dimethyl formamide 218g, its total consumption are 10 times of Diphenyl disulfide ether quality.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 17.9g, yield 78%, purity 97.9%.
Embodiment 4:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is N-Methyl pyrrolidone 218g, and its total consumption is 10 times of Diphenyl disulfide ether quality.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 16.7g, yield 73%, purity 97.8%.
Embodiment 5:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 218g, and its total consumption is 10 times of Diphenyl disulfide ether quality.Temperature of reaction is 25 ℃, and afterreaction finished in 4 hours.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 11.9g, yield 52%, purity 98.1%.
Embodiment 6:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 327g, and its total consumption is 15 times of Diphenyl disulfide ether quality.Temperature of reaction is 65 ℃, and afterreaction finished in 2.5 hours.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 19.1g, yield 83%, purity 98.1%.
Embodiment 7:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 327g, and its total consumption is 15 times of Diphenyl disulfide ether quality.Temperature of reaction is 100 ℃, and afterreaction finished in 1.5 hours.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 16.3g, yield 71%, purity 98.1%.
Embodiment 8:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 436g, and its total consumption is 20 times of Diphenyl disulfide ether quality.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 16.9g, yield 74%, purity 98.4%.
Embodiment 9:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is cesium carbonate, the quality that feeds intake 97.8g(0.3mol); Organic solvent is methyl-sulphoxide 327g, and its total consumption is 15 times of Diphenyl disulfide ether quality.
All the other are with embodiment 5, products obtained therefrom S-phenylanthranilic acid thioesters 15.4g, yield 67%, purity 98.2%.
Embodiment 10:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.0:4.0:3.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 32.6g(0.20mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 41.4g(0.3mol); Organic solvent is methyl-sulphoxide 327g, and its total consumption is 15 times of Diphenyl disulfide ether quality.
All the other are with embodiment 5, products obtained therefrom S-phenylanthranilic acid thioesters 17.4g, yield 76%, purity 97.6%.
Embodiment 11:
Disulfide, isatoic anhydride compounds, promotor and basic cpd are in molar ratio for 1.0:2.5:4.0:4.0 feeds intake, and disulfide is Diphenyl disulfide ether, the quality that feeds intake 21.8g(0.1mol); The isatoic anhydride compounds is isatoic anhydride, the quality that feeds intake 40.7g(0.25mol); Promotor is V-Brite B, the quality that feeds intake 69.6g(0.4mol); Basic cpd is salt of wormwood, the quality that feeds intake 55.2g(0.4mol); Organic solvent is methyl-sulphoxide 327g, and its total consumption is 15 times of Diphenyl disulfide ether quality.
All the other are with embodiment 1, products obtained therefrom S-phenylanthranilic acid thioesters 18.1g, yield 79%, purity 98.0%.
Embodiment 12～16
Substituting group in disulfide, the isatoic anhydride compounds raw material changes into as shown in table 1 below, feed intake for 1.0:2.5:4.0:3.0 in molar ratio with promotor and basic cpd, be warming up to 65 ℃ after adding methyl-sulphoxide, all the other steps are with embodiment 6, and the products obtained therefrom result is as shown in table 1 below:
Table 1
Claims (10)
1. a S-as shown in the formula (I) replaces the synthetic method of anthranilic acid thioes derivatives, it is characterized in that described method is: isatoic anhydride compounds as shown in the formula (II) and disulfide compound as shown in the formula (III) are raw material, in the presence of promotor and basic cpd, in inert organic solvents, fully reaction under 0 ~ 120 ℃ temperature of reaction, TLC follows the tracks of detection to reacting completely, and reaction solution obtains described S-as shown in the formula (I) through separation and purification and replaces the anthranilic acid thioes derivatives;
In formula (I) or the formula (II), R
1Be selected from one of following: the alkoxyl group of the alkyl of hydrogen, C1～C8, the alkyloyl of C1～C8, C1～C8;
In formula (I) or the formula (II), the H on phenyl ring or the aromatic nucleus is not substituted or is substituted basic R
2Replace described substituent R
2Be selected from one of following: the alkyl of C1～C8, halogen, trifluoromethyl, nitro;
In formula (I) or the formula (III), it is one of following that R is selected from: the alkyl of C2～C8, benzyl, phenyl, substituted-phenyl, and in the described substituted-phenyl, the substituting group on the phenyl ring is the alkyl of C1～C8, alkoxyl group, halogen or the trifluoromethyl of C1～C8;
Described halogen is F, Cl, Br or I;
It is one of following that described promotor is selected from: S-WAT, sodium bisulfite, V-Brite B, rongalite, Sodium Pyrosulfite, Sulfothiorine;
The ratio of the amount of substance of the disulfide compound shown in the described formula (III), isatoic anhydride compounds as shown in the formula (II), promotor, basic cpd is 1.0:1.0～4.0:1.0～6.0:2.5 ~ 4.5.
2. the method for claim 1 is characterized in that described R
1Be hydrogen or methyl.
3. the method for claim 1 is characterized in that the H on phenyl ring or the aromatic nucleus is not substituted or is substituted basic R in described formula (I) or the formula (II)
2Replace described substituent R
2For one of following: chlorine, methyl.
4. the method for claim 1 is characterized in that described R is one of following: benzyl, phenyl, substituted-phenyl, in the described substituted-phenyl, it is one of following that the substituting group on the phenyl ring is selected from: methyl or chlorine.
5. the method for claim 1, it is characterized in that described inert organic solvents be following one or more mixing: chlorobenzene, N, dinethylformamide, toluene, methyl-sulphoxide, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane, ethyl acetate, N-Methyl pyrrolidone, tetracol phenixin, methylene dichloride, acetonitrile.
6. the method for claim 1 is characterized in that described basic cpd is yellow soda ash, salt of wormwood, cesium carbonate, sodium bicarbonate, sodium-acetate, sodium hydroxide or potassium tert.-butoxide.
7. the method for claim 1 is characterized in that described temperature of reaction is 25 ~ 100 ℃.
8. the method for claim 1, the quality consumption that it is characterized in that described inert organic solvents is 5～25 times of the quality of as shown in the formula (III) disulfide compound.
9. the method for claim 1, it is characterized in that described reaction solution through separation purification method is: after reaction finishes, reaction solution adds the saturated common salt water washing, separate and get organic layer, dry rear steaming desolventizes and namely gets described S-replacement anthranilic acid thioes derivatives as shown in the formula (I).
10. the method for claim 1, the synthetic method that it is characterized in that described S-replacement anthranilic acid thioes derivatives is carried out according to the following steps: as shown in the formula (II) isatoic anhydride compounds and promotor are dissolved in the inert organic solvents, stir and drip under 25 ~ 100 ℃ of temperature with the disulfide compound as shown in the formula (III) of same inert organic solvents dissolving and the solution of basic cpd, dropwise insulation reaction under rear 25 ~ 100 ℃ of temperature, the TLC tracking monitor is to reacting completely, reaction solution adds the saturated common salt water washing, separate and get organic layer, dry rear steaming desolventizes and namely gets described S-replacement anthranilic acid thioes derivatives as shown in the formula (I);
Described promotor is V-Brite B or rongalite;
The ratio of the amount of substance of the disulfide compound shown in the described formula (III), isatoic anhydride compounds as shown in the formula (II), promotor, basic cpd is 1.0:1.5～3.0:3.0～4.5:3 ~ 4;
Described inert organic solvents be following one or more mixing: DMF, methyl-sulphoxide, N-Methyl pyrrolidone;
The total quality consumption of described inert organic solvents is 5～25 times of quality of disulfide compound as shown in the formula (III);
Described basic cpd is salt of wormwood or cesium carbonate.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107629028A (en) * | 2017-10-31 | 2018-01-26 | 沅江华龙催化科技有限公司 | A kind of method based on intermolecular ring-closure reaction synthesis furan derivatives |
| CN107739353A (en) * | 2017-10-31 | 2018-02-27 | 沅江华龙催化科技有限公司 | A kind of synthetic method of 2,3,5 trisubstituted furans |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107629028A (en) * | 2017-10-31 | 2018-01-26 | 沅江华龙催化科技有限公司 | A kind of method based on intermolecular ring-closure reaction synthesis furan derivatives |
| CN107739353A (en) * | 2017-10-31 | 2018-02-27 | 沅江华龙催化科技有限公司 | A kind of synthetic method of 2,3,5 trisubstituted furans |
| CN107629028B (en) * | 2017-10-31 | 2019-05-03 | 沅江华龙催化科技有限公司 | A method of furan derivatives are synthesized based on intermolecular ring-closure reaction |
| CN107739353B (en) * | 2017-10-31 | 2019-09-17 | 沅江华龙催化科技有限公司 | A kind of synthetic method of 2,3,5- trisubstituted furans |
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Application publication date: 20130130 |