CN1847231A - Process of preparing aromatic ring substituted ixooxazoline compound - Google Patents
Process of preparing aromatic ring substituted ixooxazoline compound Download PDFInfo
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- CN1847231A CN1847231A CN 200510046262 CN200510046262A CN1847231A CN 1847231 A CN1847231 A CN 1847231A CN 200510046262 CN200510046262 CN 200510046262 CN 200510046262 A CN200510046262 A CN 200510046262A CN 1847231 A CN1847231 A CN 1847231A
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Abstract
The present invention discloses process of preparing aromatic ring substituted isooxazoline compound. In the presence of Lewis acid or organic acid catalyst and in organic solvent, nitrone and single substituted aryl ethylene are reacted at the temperature from 80 deg.c to the reflux temperature for 4-10 hr. The preparation process of the present invention has product yield over 85 % and the product has purity over 90 %. The preparation process is environment friendly and can meet the requirement of industrial production of farm germicide.
Description
Technical field
The present invention relates to a kind of method that aromatic ring replaces the De isoxazoline compounds for preparing.
Background technology
Chinese patent CN1280767A has reported the heterocyclic substituted De isoxazoline compounds as sterilant.The heterocyclic substituted De isoxazoline compounds of being announced in the document prepares by following reaction formula:
In the formula: X is selected from N or CH, R, R
1, R
2, R
3, R
4And R
5Be selected from hydrogen, alkyl, alkylhalide group, thiazolinyl, alkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclic radical independently of one another.
Reaction is made solvent with benzene, toluene or chlorobenzene, finishes to the reaction solution reflux temperature for 50 ℃.
Discover that further some aromatic ring as following general formula replaces the De isoxazoline compounds and also can prepare according to above method:
In the formula: X is selected from hydrogen, halogen, cyano group, nitro, (C
1-C
4) alkoxyl group, (C
1-C
4) alkyl or halogen (C
1-C
4) alkyl, n is the integer of 1-5; Y is selected from carbon or nitrogen; R, R
1, R
2, R
3, R
4And R
5Independently be selected from hydrogen, alkyl, alkylhalide group, thiazolinyl, alkynyl, alkoxyl group, cycloalkyl or aryl separately.
Such compound with fungicidal activity has been applied for Chinese patent, application number 200410020467.9.
But, shortcomings such as this method exists that reaction is not easy to carry out, reaction yield low (only can reach about 20%), product content are low, be only applicable to preparation new compound in the laboratory, can not satisfy the needs that commercial scale production has the isoxazoline compounds of high biological activity, therefore limit the commercial development prospect of this series bactericidal agent.
Summary of the invention
The objective of the invention is to develop the method for the safe aromatic ring substituted isoxazolines compounds of preparation shown in general formula (I) of a kind of high yield, high quality and reaction.
In the formula: X is N or C, R
1Be selected from hydrogen, C
1-C
5Alkyl, halogen C
1-C
5Alkyl, C
2-C
5Thiazolinyl, halogen C
2-C
5Thiazolinyl, C
2-C
5Alkynyl or halogen C
2-C
5Alkynyl, R
2Be aryl, Y is hydrogen, halogen, cyano group, nitro, C
1-C
4Alkoxyl group, C
1-C
4Alkyl or halogen C
1-C
4Alkyl, n are the integer of 1-5.
Have now found that add suitable catalyzer and can promote 1 in the process of preparation general formula (I) compound, finishing of 3-Dipolar Cycloaddition makes reaction obtain gratifying beyond thought outstanding effect.Simultaneously the catalyzer of Jia Ruing also can be used as nitrone (II) stablizer, reaction can be finished under the condition of safety, existing reaction yield is low in the prior art, product content is low and produce uneasy congruent problem thereby solved.
Technical scheme of the present invention is as follows:
The invention provides a kind of method that aromatic ring replaces the De isoxazoline compounds for preparing, reaction is a raw material with nitrone (II) and single substituted aryl ethene (III), and reaction formula is as follows:
The suitable catalyzer of reaction is Lewis acid or organic acid, and the add-on of catalyzer is a 0.05-1.0 moles/mole nitrone.
Be reflected in the organic solvent in 80 ℃ and finished in 4-10 hour to the reaction solution reflux temperature.
More preferably catalyzer is selected from aluminum chloride, tin tetrachloride, boron trifluoride, acetate, diacetyl oxide or propionic acid etc., and add-on is a 0.05-0.8 moles/mole nitrone; Further preferred catalyzer is selected from acetate or diacetyl oxide, and add-on is a 0.1-0.5 moles/mole nitrone.
More preferably solvent is benzene, toluene or dimethylbenzene, and further preferred solvent is a dimethylbenzene.The consumption of solvent is advisable with 1-5 liter/mole nitrone.Preferred temperature is the reaction solution reflux temperature, so both convenient control reaction, suitable fast reaction speed again.For example use dimethylbenzene to do the solvent refluxing reaction, make catalyzer, can effectively shorten the reaction times, improve product yield and quality greatly with acetate.
Reacting raw materials used part has commercially available or can prepare according to currently known methods, for example prepare nitrone (II) with reference to Chinese patent CN1280767A reported method, with reference to Synthesis of ar-nitrostyrenes, Aust.J.Chem.197326 (9): the 2067-2069 reported method prepares alkene (III).
Usually order of addition(of ingredients) is: add solvent, nitrone (II), catalyzer earlier, drip alkene (III) then under reflux state.For preventing olefinic polymerization in the reaction process, generally add the stopper (in the alkene weight that adds) of 0.05%-1%.The stopper that prevents olefinic polymerization commonly used all can use.Test finds that this reacts optimum stopper is p-ten.-butylcatechol.Stopper both can add in reaction process, also can add in advance in the raw material olefin (III).
According to preparation method provided by the invention, can improve the product yield (bringing up to more than 85%) of the aromatic ring substituted isoxazolines compounds shown in the general formula (I) greatly from about 20% of prior art.Product content can reach more than 90%, need not the further refining needs that can satisfy the commercial scale production disinfectant use in agriculture.The production technique safety and environmental protection can be referred to as a kind of very significant green synthesis method simultaneously.
Embodiment
Following examples are used to further specify the present invention.But the present invention is not limited in following embodiment.
Embodiment 1
2-methyl-3-(4-p-methoxy-phenyl)-5-(synthesizing of 3-p-methoxy-phenyl) isoxazoline:
100 milliliters of there-necked flasks N-methyl-C-p-methoxyphenyl nitrone 3.4 grams (0.02 mole) that feed intake, dimethylbenzene (30 milliliters) stirs, and drips 10% diacetyl oxide xylene solution (10 gram), pH value of solution=6-7, add p-ten.-butylcatechol (1.5 milligrams), slowly be warming up to backflow, drip meta-methoxy vinylbenzene 2.8 grams (0.0202 mole), added in about 15 minutes, continue back flow reaction, liquid chromatography trace analysis control reaction end, the about 4-5 of total reaction time hour.Cooling, reaction solution is deviate from toluene and is got yellow oil 5.8 grams (content 93.8%), yield 90.9% with 50 milliliters of washed twice of 2% sodium bicarbonate aqueous solution.Analytical results is as follows:
Nuclear-magnetism:
1H-NMR(CDCI
3，300MHz)δ2.68(S?3H)3.81(S?3H)，3.83(S?3H)，2.36-2.44，2.99-3.08(2m1H)，2.54-2.59，2.60-2.72(2m?1H)，5.21(t?J＝7.8Hz?1H)，3.78(m?1H)，6.84(m?1H)，6.90(m?1H)，7.00(m?1H)，7.04(m?1H)，7.29(m?3H)。
13C-NMR(CDCI
3，300MHz)δ42.96(43.46)，48.38，55.05，72.59(73.20)，77.85(78.43)，111.3，112.9，114.2，118.7，128.6，129.3，130.7，142.7(144.9)，159.1，159.6。
Infrared: IR (NaCI) 2980,2920,1620,1520,1250,1040,840cm
-1
Mass spectrum: MS (m/z) 300 ([M
++ 1], 100), 253 (6), 166 (6), 150 (8).
Ultimate analysis: C
18H
21NO
3Theoretical value: C 72.24, H 7.02, and O 16.05, and N 4.68;
Measured value: C 72.00, H 7.26, and O 16.08, and N 4.64.
Embodiment 2
2,3-dimethyl-3-(3-pyridyl)-5-(synthesizing of 4-chloro-phenyl-) isoxazoline:
100 milliliters of there-necked flasks C that feeds intake, N-dimethyl-C-(3-pyridyl) nitrone 3.1 grams (0.02 mole), dimethylbenzene (30 milliliters), stir, drip 10% acetate xylene solution (8.5 gram), pH value of solution=6.8 add p-ten.-butylcatechol (1.5 milligrams), slowly be warming up to backflow, dropping added chloro-styrene 2.9 grams (0.0202 mole) in about 20 minutes, continued back flow reaction, liquid chromatography trace analysis control reaction end, the about 4-5 of total reaction time hour.Cooling adds 10% aqueous hydrochloric acid (20 milliliters), tells water, and being neutralized to the pH value of solution value with 30% sodium hydroxide is 9, and three times (20 milliliters/time) of toluene extraction are deviate from toluene and got brown solidliquid mixture 5.6 grams (content 92.8%), yield 90.1%.Analytical results is as follows:
Nuclear-magnetism:
1H-NMR(CDCI
3，300MHz)：δ1.58(S?3H)，2.64(S?3H)，2.36，2.97，2.89，2.56(4dd?2H)，5.01，5.25(t，dd?1H)，7.96(d1H)，8.53(d1H)，8.82(d1H)，7.14-7.34(m5H)。
13C-NMR(CDCI
3，300MHz)22.02，39.01，51.58，67.88，77.00(76.57，77.42)，123.3，127.5，128.4，133.4，134.4，139.5(140.2)，148.2(148.0)，142.7(144.9)，159.1，159.6。
Infrared: IR (NaCI) 2990,2940,1570,1420,1090,820,720cm
-1
Ultimate analysis: C
16H
17CIN
2O theoretical value: C 66.55, H 5.89, and O 5.55, and N 9.71;
Measured value: C 66.56, H 5.86, and O 5.58, and N 9.73.
Reference examples:
According to Chinese patent CN1280767A reported method, preparation embodiment 2 described compounds: 2,3-dimethyl-3-(3-pyridyl)-5-(4-chloro-phenyl-) isoxazoline
Add 31 gram nitrones (0.2 mole), 29 grams in 500 milliliters of there-necked flasks to chloro-styrene (0.202 mole) and 200 milliliters of toluene, reflux, liquid chromatography follow-up control reaction end, about 9.5 hours of total reaction time.Cooling after reaction is finished, product solution is with 200 milliliter of 10% hcl as extraction agent twice, with 10% sodium hydroxide adjust pH to 9.With 200 milliliters of toluene extractions 3 times.Merge the organic phase precipitation, get brown oil 32 grams, product content 43.6%, reaction yield 24.2%, 3-acetylpyridine content 51.4%.
Thick product 32 grams, 80 milliliters of methyl alcohol add 12 gram N-methyl hydroxylamine vitriol and 21 gram anhydrous sodium acetates, stirring at room, liquid chromatography trace analysis control reaction end, about 24 hours of total reaction time in 250 milliliters of there-necked flasks.Cooling is filtered.Add 500 ml waters and 100 milliliters of toluene in the filtrate, phase-splitting, organic phase washes with water.Get brown solidliquid mixture 15 grams (content 88.5%) behind the precipitation, yield 23%.Be the purpose product by analysis.
Embodiment 3
2,3-dimethyl-3-(3-pyridyl)-5-(synthesizing of 4-chloro-phenyl-) isoxazoline: (reaction is with embodiment 2)
3000 liters of enamel stills C that feeds intake, 156 kilograms of nitrones of N-dimethyl-C-(3-pyridyl) (1000 moles), dimethylbenzene (1000 kilograms), stir, drip 10% acetate xylene solution (100 kilograms), pH value of solution=6.8 add p-ten.-butylcatechol (80 gram), slowly be warming up to backflow, dropping added 147 kilograms of chloro-styrenes (1020 moles) in 30 minutes, continued back flow reaction, liquid chromatography trace analysis control reaction end, total reaction time 4.8 hours.Reaction solution is reduced to room temperature, adds 10% aqueous hydrochloric acid (450 kilograms), tells water, being neutralized to the pH value of solution value with 30% sodium hydroxide is 9, toluene extraction (200 kilograms three times) is deviate from toluene and is got 291 kilograms of brown solidliquid mixtures (content 90.6%), yield 91.4%.Analytical results is with embodiment 2.
Embodiment 4
2-methyl-3-(4-p-methoxy-phenyl)-5-(synthesizing of 4-pyridyl) isoxazoline:
100 milliliters of there-necked flasks drop into N-methyl-C-(4-p-methoxy-phenyl) nitrone 3.4 grams (0.02 mole), toluene (20 milliliters), stir, drip 10% acetate toluene solution (6.5 gram) and, add p-ten.-butylcatechol (2.0 milligrams) to pH value of solution=7.0, slowly be warming up to backflow, drip 4-pyridyl ethene 2.2 grams (0.0202 mole), added in about 20 minutes, continue back flow reaction, liquid chromatography trace analysis control reaction end, the about 9-10 of total reaction time hour.Reaction solution is with 50 milliliters of washed twice of 2% sodium bicarbonate aqueous solution.Add 10% aqueous hydrochloric acid (20 milliliters), tell water, being neutralized to the pH value of solution value with 30% sodium hydroxide is 9, and toluene is deviate from toluene extraction (20 milliliters three times), yellow oil 5.2 grams (content 91.2%), yield 87.8%.Analytical results is as follows:
Nuclear-magnetism:
1H-NMR(CDCI
3，300MHz)：δ2.66，2.70(2S?3H)，3.78，3.81(2S?3H)，2.26-2.35，3.11-3.21(2m1H)，2.48-2.54，2.70-2.84(2m?1H)，3.65(m?1H)，5.20(q?J＝6.6Hz，8.4Hz?1H)，6.84，6.90(2dd?J＝8.7Hz2H)，7.20，7.30(2dd?J＝8.7Hz?2H)，7.26-7.39(m?2H)，8.58-8.61(m?2H)。
13C-NMR(CDCI
3，300MHz)43.06，47.3(48.0)，55.18，72.23(73.35)，76.17(76.91)，114.1，120.7，122.7，129.9，130.3，150.0，159.3。
Infrared: IR (NaCI) 2980,2920,1600,1520,1250,1040,840cm
-1
Mass spectrum: MS m/z (%) 271 ([M
++ l], 64), 166 (100), 106 (8), 240 (4).
Embodiment 5
Synthesizing of 2-methyl-3-p-methoxyphenyl-5-rubigan isoxazoline:
100 milliliters of there-necked flasks N-methyl-C-p-methoxyphenyl nitrone 3.4 grams (0.02 mole) that feed intake, toluene (20 milliliters) stirs, and drips 10% diacetyl oxide toluene solution (11 gram), pH value of solution=6.8, add p-ten.-butylcatechol (2.0 milligrams), slowly be warming up to backflow, drip chloro-styrene 2.9 grams (0.0202 mole), added in about 15 minutes, continue back flow reaction, liquid chromatography trace analysis control reaction end, the about 9-10 of total reaction time hour.Cooling, reaction solution is deviate from toluene and is got faint yellow solid 5.8 grams (content 92.8%), yield 88.7%, fusing point 80-90 ℃ with 50 milliliters of washings of 2% sodium bicarbonate aqueous solution three times.Analytical results is as follows:
Nuclear-magnetism:
1H-NMR(CDCI
3，300MHz)：δ2.3-2.36，3.04-3.13(2m?1H)，2.47-2.56，2.65-2.77(2m?1H)，2.66，2.67(2S?3H)，3.65-3.7(m?1H)，3.78，3.81(2S?3H)，5.22(t?J＝8.41H)，6.86，6.90(2dd?J＝8.7Hz2H)，7.24-7.30(m?2H)，7.30-7.43(m?4H)。
13C-NMR(CDCI
3，300MHz)42.99(43.35)，47.50(48.52)，55.15，72.68(73.35)，77.25(77.90)，114.00，127.23，127.84，128.46，128.53，128.70，128.77，130.39，130.73，132.77，133.41。
Infrared: IR (KBr) 2980,2920,1620,1520,1300,1260,1180,1040,830cm
-1
Mass spectrum: MS m/z (%) 304 ([M
++ 1], 100), 286 (3), 257 (7), 170 (10).
Ultimate analysis: C
17H
18CINO
2Theoretical value: C 67.22, H 5.93, and O 10.54, and N 4.61;
Measured value: C 67.19, H 5.96, and O 10.58, and N 4.57.
Claims (2)
1, a kind of method for preparing aromatic ring replacement De isoxazoline compounds, reaction is a raw material with nitrone (II) and single substituted aryl ethene (III), in the presence of Lewis acid or organic acid catalyst, in organic solvent, finish for 80 ℃ to reflux temperature 4-10 hour, reaction formula is as follows:
In the formula: X is N or C, R
1Be selected from hydrogen, C
1-C
5Alkyl, halogen C
1-C
5Alkyl, C
2-C
5Thiazolinyl, halogen C
2-C
5Thiazolinyl, C
2-C
5Alkynyl or halogen C
2-C
5Alkynyl, R
2Be aryl, Y is hydrogen, halogen, cyano group, nitro, C
1-C
4Alkoxyl group, C
1-C
4Alkyl or halogen C
1-C
4Alkyl, n are the integer of 1-5;
The add-on of catalyzer is a 0.05-1.0 moles/mole nitrone.
2, according to the described preparation method of claim 1, it is characterized in that: described catalyzer is selected from acetate or diacetyl oxide, and add-on is a 0.1-0.5 moles/mole nitrone; Described solvent is selected from toluene or dimethylbenzene.
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|---|---|---|---|
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|---|---|---|---|
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|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061304A (en) * | 2015-06-05 | 2015-11-18 | 沈阳科创化学品有限公司 | Method for preparing isoxazoline compound and intermediate thereof |
| CN105085502A (en) * | 2015-06-05 | 2015-11-25 | 沈阳科创化学品有限公司 | Compound with high biological activity, preparation method therefore and pesticide composition |
| CN106866541A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method for preparing benzimidazoles derivative |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091444C (en) * | 1999-07-14 | 2002-09-25 | 沈阳化工研究院 | Heterocycle substituted isoxazoline compounds used as disinfectant |
-
2005
- 2005-04-15 CN CNB2005100462622A patent/CN100389110C/en active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061304A (en) * | 2015-06-05 | 2015-11-18 | 沈阳科创化学品有限公司 | Method for preparing isoxazoline compound and intermediate thereof |
| CN105085502A (en) * | 2015-06-05 | 2015-11-25 | 沈阳科创化学品有限公司 | Compound with high biological activity, preparation method therefore and pesticide composition |
| CN106866541A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method for preparing benzimidazoles derivative |
| CN106866541B (en) * | 2015-12-11 | 2019-03-01 | 中国科学院大连化学物理研究所 | A method of preparing benzimidazoles derivative |
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|---|---|
| CN100389110C (en) | 2008-05-21 |
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