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Process of preparing aromatic ring substituted ixooxazoline compound

A technology for isoxazolines and compounds, which is applied in the field of preparation of isoxazolines substituted by aromatic rings, can solve the problems of low product content, low reaction yield, and limited prospect of commercial development of fungicides, etc., to improve product quality The effect of yield and production process safety and environmental protection

Active Publication Date: 2008-05-21
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] However, this method has disadvantages such as difficult reaction, low reaction yield (only about 20%), and low product content. It is only applicable to the preparation of new compounds in the laboratory, and cannot meet the industrial scale production of heterogeneous compounds with high biological activity. The need for oxazoline compounds, thus limiting the commercial development prospects of this type of fungicide

Method used

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  • Process of preparing aromatic ring substituted ixooxazoline compound
  • Process of preparing aromatic ring substituted ixooxazoline compound
  • Process of preparing aromatic ring substituted ixooxazoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 2-methyl-3-(4-methoxyphenyl)-5-(3-methoxyphenyl)isoxazoline:

[0028]

[0029] 100 milliliters of there-necked flasks feed 3.4 grams (0.02 mole) of N-methyl-C-p-methoxyphenylnitrone, xylene (30 milliliters), stir, add dropwise 10% acetic anhydride xylene solution (10 grams), Solution pH = 6-7, add p-tert-butylcatechol (1.5 mg), slowly warm up to reflux, drop m-methoxystyrene 2.8 g (0.0202 moles), add about 15 minutes, continue to reflux reaction, liquid Phase chromatography tracking analysis controls the reaction end point, and the total reaction time is about 4-5 hours. The temperature was lowered, and the reaction solution was washed twice with 50 ml of 2% sodium bicarbonate aqueous solution, and the toluene was removed to obtain 5.8 g of a yellow oil (content 93.8%), yield 90.9%. The analysis results are as follows: NMR:

[0030] 1 H-NMR (CDCI 3 , 300MHz) δ 2.68(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),...

Embodiment 2

[0037] Synthesis of 2,3-dimethyl-3-(3-pyridyl)-5-(4-chlorophenyl)isoxazoline:

[0038]

[0039] 100 ml three-necked flask was charged with C, 3.1 g (0.02 moles) of N-dimethyl-C-(3-pyridyl) nitrone, xylene (30 ml), stirred, and added dropwise 10% xylene acetic acid solution (8.5 g ), the solution pH=6.8, add p-tert-butylcatechol (1.5 mg), slowly warm up to reflux, drop 2.9 grams (0.0202 moles) of p-chlorostyrene, add it in about 20 minutes, continue the reflux reaction, liquid chromatography Follow-up analysis controls the reaction end point, and the total reaction time is about 4-5 hours. Cool down, add 10% hydrochloric acid aqueous solution (20 ml), separate the water phase, neutralize with 30% sodium hydroxide to a pH value of 9, extract with toluene three times (20 ml / time), remove toluene to obtain 5.6 g of a brown solid-liquid mixture (content 92.8%), yield 90.1%. The analysis results are as follows:

[0040] NMR:

[0041]1 H-NMR (CDCI 3 , 300MHz): δ 1.58(S 3H), 2...

Embodiment 3

[0051] 2, the synthesis of 3-dimethyl-3-(3-pyridyl)-5-(4-chlorophenyl) isoxazoline: (reaction is the same as Example 2)

[0052] 3000 liters of enamel kettle feed C, 156 kilograms (1000 moles) of N-dimethyl-C-(3-pyridyl) nitrone, xylene (1000 kilograms), stir, add dropwise 10% xylene acetic acid solution (100 kilograms ), solution pH=6.8, add p-tert-butylcatechol (80 grams), slowly heat up to reflux, drop 147 kilograms (1020 moles) of p-chlorostyrene, add in 30 minutes, continue the reflux reaction, liquid chromatography tracking The analysis controls the reaction end point, and the total reaction time is 4.8 hours. The reaction solution was cooled to room temperature, added 10% hydrochloric acid aqueous solution (450 kg), separated the water phase, neutralized with 30% sodium hydroxide until the pH value of the solution was 9, extracted with toluene (200 kg three times), and the toluene was removed to obtain a brown solid-liquid mixture 291 kg (90.6% content), yield 91.4%. ...

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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 [0001] The invention relates to a method for preparing aromatic ring substituted isoxazoline compounds. Background technique [0002] Chinese patent CN1280767A reports heterocyclic substituted isoxazoline compounds used as fungicides. The heterocyclic substituted isoxazoline compounds disclosed in this document are prepared according to the following reaction formula: [0003] [0004] In the formula: X is selected from N or CH, R, R 1 , R 2 , R 3 , R 4 and R 5 Each is independently selected from hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, or heterocyclyl. [0005] The reaction takes benzene, toluene or chlorobenzene as solvent, and is completed at 50°C to the reflux temperature of the reaction solution. [0006] Further studies have found that some aromatic ring-substituted isoxazoline compounds such as the following general formula can also be prepared according to the above method: [...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/02C07D401/04
Inventor 程春生邹本勤李鹏盖永明彭军
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD