CN102532014A - Preparation method of 4-trifluoroethoxyl pyridine-N-oxide derivative - Google Patents
Preparation method of 4-trifluoroethoxyl pyridine-N-oxide derivative Download PDFInfo
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- CN102532014A CN102532014A CN 201010618046 CN201010618046A CN102532014A CN 102532014 A CN102532014 A CN 102532014A CN 201010618046 CN201010618046 CN 201010618046 CN 201010618046 A CN201010618046 A CN 201010618046A CN 102532014 A CN102532014 A CN 102532014A
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- pyridine
- trifluoro ethoxy
- oxide
- oxide derivative
- trifluoroethoxyl
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Abstract
The invention provides a preparation method of a 4-trifluoroethoxyl pyridine-N-oxide derivative. In the method, 4-(2,2,2-trifluoroethoxyl)pyridine oxide, 2,3-dimethyl-2-(2,2,2-trifluoroethoxyl)pyridine oxide and 2-methyl-3-chlorin-4-(2,2,2-trifluoroethoxyl)pyridine oxide are prepared by taking a readily-available 4-nitro-N-pyridine oxide derivative and 2,2,2-trifluoroethanol as raw materials under the action of a strong alkali. The reaction conditions are mild, and operation is simple.
Description
Technical field
The present invention relates to the fluorine chemical field, be specifically related to the compound method of 4-trifluoro ethoxy pyridine-N-oxide derivative.
Background technology
The compound method of 4-trifluoro ethoxy pyridine-N-oxide derivative mainly contains following several kinds: with 4-NPO verivate and various trifluoro ethoxy ester (as: trifluoro ethoxy sulphonate; Trifluoro ethoxy benzene sulfonates etc.) be raw material, HMPA is that solvent and sodium hydride reaction are synthetic; With phenol and trifluoro iodoethane is starting raw material, and DMSO is a solvent, reaction under the effect of catalyzer Potassium monofluoride; With halogeno-benzene and sodium hydride, the trifluoroethanol reaction is a solvent with DMF; With nitropyridine and trifluoroethanol, salt of wormwood is raw material, and acetonitrile is a solvent, under the Tetrabutylammonium bromide katalysis, reacts.In the above method, some raw material (like the trifluoro ethoxy ester) preparation difficulty is difficult for obtaining; Some raw material ratio is expensive, not suitable for mass production.
Summary of the invention
The object of the present invention is to provide from the method for the synthetic 4-NPO verivate of the initial catalysis of the reagent that is easy to obtain.Have now found that the preparation method of a kind of 4-trifluoro ethoxy pyridine-N-oxide derivative, it is a raw material with 4-NPO verivate and 2,2,2 tfifluoroethyl alcohol, under the highly basic effect, makes 4-trifluoro ethoxy pyridine-N-oxide derivative.Wherein, described 4-trifluoro ethoxy pyridine-N-oxide derivative is 4-(2,2, a 2-trifluoro ethoxy) pyridine oxide.Wherein, described 4-trifluoro ethoxy pyridine-the N-oxide derivative is 2,3-dimethyl--2-(2,2, the 2-trifluoro ethoxy) pyridine oxide.Wherein, described 4-trifluoro ethoxy pyridine-N-oxide derivative is 2-methyl-3-chloro-4-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
Preferably, in the organic solvent that is selected from halogenated or not halogenated aliphatic series, alicyclic, aromatic hydrocarbon, carry out said reaction, the preferred hexane of said organic solvent, hexanaphthene, methylcyclohexane, toluene, mono chloro benzene, glycerine.
According to batch mode, optional solvent, reactant and catalyzer are infeeded in the reactor drum.Be heated to the temperature that preceding text limit.Apply desirable pressure and maintenance.When reaction finishes, according to the solid/liquid separation technique of routine, preferably via filtration, separating catalyst.Reclaim the product that is obtained by routine, preferably perhaps pass through liquid/liquid extraction through distillation.
Embodiment
Provide below and be used to illustrate and nonrestrictive exemplary of the present invention.
In an embodiment, transformation efficiency is corresponding to the ratio of the substrate mole number that transforms with the substrate mole number that infeeds, and given yield is corresponding to the ratio of the product mole number that forms with the substrate mole number that infeeds.
Embodiment 1
In three mouthfuls of reaction flasks, add the 40ml trifluoroethanol, stir, add an amount of solid sodium hydroxide, after the band dissolving, add 0.06ml 4-nitropyridine-N-pyridine oxide; Reflux 8h, decompression boils off excessive trifluoroethanol, and cooling is poured in the separating funnel; Add 20ml water dissolution solid, use the 40ml*3 chloroform extraction, use anhydrous magnesium sulfate drying, trichloromethane is removed in decompression, cooling; Separate out solid, filter, washing, drying gets thick product; Carry out recrystallization with ETHYLE ACETATE, obtain product 4-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
Embodiment 2
In three mouthfuls of reaction flasks, add the 40ml trifluoroethanol, stir, add an amount of solid sodium hydroxide, after the band dissolving, add 0.06ml 2,3-dimethyl--2-nitropyridine-N-pyridine oxide; Reflux 8h, decompression boils off excessive trifluoroethanol, and cooling is poured in the separating funnel; Add 20ml water dissolution solid, use the 40ml*3 chloroform extraction, use anhydrous magnesium sulfate drying, trichloromethane is removed in decompression, cooling; Separate out solid, filter, washing, drying gets thick product; Carry out recrystallization with ETHYLE ACETATE, obtain product 2,3-dimethyl--2-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
Embodiment 3
In three mouthfuls of reaction flasks, add the 40ml trifluoroethanol, stir, add an amount of solid sodium hydroxide, after the band dissolving, add 0.06ml 2-methyl-3-chloro-4-nitropyridine-N-pyridine oxide; Reflux 8h, decompression boils off excessive trifluoroethanol, and cooling is poured in the separating funnel; Add 20ml water dissolution solid, use the 40ml*3 chloroform extraction, use anhydrous magnesium sulfate drying, trichloromethane is removed in decompression, cooling; Separate out solid, filter, washing, drying gets thick product; Carry out recrystallization with ETHYLE ACETATE, obtain product 2-methyl-3-chloro-4-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
Claims (4)
1. the preparation method of 4-trifluoro ethoxy pyridine-N-oxide derivative, it is a raw material with 4-NPO verivate and 2,2,2 tfifluoroethyl alcohol, under the highly basic effect, makes 4-trifluoro ethoxy pyridine-N-oxide derivative.
2. the method for claim 1 is characterized in that, described 4-trifluoro ethoxy pyridine-N-oxide derivative is 4-(2,2, a 2-trifluoro ethoxy) pyridine oxide.
3. the method for claim 1 is characterized in that, described 4-trifluoro ethoxy pyridine-the N-oxide derivative is 2,3-dimethyl--2-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
4. the method for claim 1 is characterized in that, described 4-trifluoro ethoxy pyridine-N-oxide derivative is 2-methyl-3-chloro-4-(2,2, the 2-trifluoro ethoxy) pyridine oxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010618046 CN102532014A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 4-trifluoroethoxyl pyridine-N-oxide derivative |
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| CN 201010618046 CN102532014A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 4-trifluoroethoxyl pyridine-N-oxide derivative |
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| CN102532014A true CN102532014A (en) | 2012-07-04 |
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| CN 201010618046 Pending CN102532014A (en) | 2010-12-30 | 2010-12-30 | Preparation method of 4-trifluoroethoxyl pyridine-N-oxide derivative |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104628637A (en) * | 2015-03-06 | 2015-05-20 | 西安近代化学研究所 | Refining method of 2,6-diamino-3,5-dinitropyridine-1-oxide |
| CN113880693A (en) * | 2021-11-12 | 2022-01-04 | 盐城迪赛诺制药有限公司 | Method for recovering trifluoroethanol in multi-component solvent |
-
2010
- 2010-12-30 CN CN 201010618046 patent/CN102532014A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104628637A (en) * | 2015-03-06 | 2015-05-20 | 西安近代化学研究所 | Refining method of 2,6-diamino-3,5-dinitropyridine-1-oxide |
| CN104628637B (en) * | 2015-03-06 | 2017-03-01 | 西安近代化学研究所 | A kind of process for purification of 2,6 diaminourea, 3,5 di nitryl pyridine 1 oxide |
| CN113880693A (en) * | 2021-11-12 | 2022-01-04 | 盐城迪赛诺制药有限公司 | Method for recovering trifluoroethanol in multi-component solvent |
| CN113880693B (en) * | 2021-11-12 | 2022-08-23 | 盐城迪赛诺制药有限公司 | Method for recovering trifluoroethanol in multi-component solvent |
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Application publication date: 20120704 |