CN112409289A - Synthetic method of 2-chloro-5-chloromethyl thiazole - Google Patents
Synthetic method of 2-chloro-5-chloromethyl thiazole Download PDFInfo
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- CN112409289A CN112409289A CN202010981058.4A CN202010981058A CN112409289A CN 112409289 A CN112409289 A CN 112409289A CN 202010981058 A CN202010981058 A CN 202010981058A CN 112409289 A CN112409289 A CN 112409289A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
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Abstract
The invention is applicable to the field of chemical synthesis, and provides a synthesis method of 2-chloro-5-chloromethyl thiazole, which comprises the following steps: placing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent for mixing to obtain a mixed solution; adding an oxidant into the mixed solution for reaction to obtain a reaction solution; standing and layering the reaction solution to obtain an organic layer; and (3) cleaning the organic layer, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole. The synthesis method provided by the invention simplifies the reaction steps, the acidity of the wastewater after the reaction is very weak, the wastewater only needs slightly adjusted alkali, the salt content is low, the wastewater is easy to treat, meanwhile, the hydrochloric acid is also a relatively abundant raw material in the market and is easy to obtain, the hydrochloric acid is not suitable for highly toxic chlorine gas in the reaction process, the chlorine gas is generated on site through a reaction system and then reacts in time, and the hidden danger of chlorine gas leakage does not exist.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a synthetic method of 2-chloro-5-chloromethyl thiazole.
Background
The 2-chloro-5-chloromethyl thiazole is an important intermediate for synthesizing pesticides thiamethoxam, clothianidin, dinotefuran and ritonavir. Thiamethoxam is used as a second generation nicotine high-efficiency low-toxicity insecticide with a brand-new structure, has the characteristics of low dosage, broad spectrum, high efficiency and the like, and becomes a new hotspot of the current pesticide development; meanwhile, the demand of ritonavir as an important intermediate is also increasing year by year. Therefore, the 2-chloro-5-chloromethyl thiazole has extremely high application prospect.
Currently, the synthesis methods of 2-chloro-5-chloromethylthiazole include the following methods:
1. the chlorine is directly reacted with 1-isothiocyanato-2-chloro-2-propylene to synthesize the compound. The chlorine gas is extremely toxic, so the pollution is serious;
2. sulfuryl chloride is adopted as a raw material. The method is not suitable for industrial production because the tail gas contains sulfur dioxide and is difficult to treat.
Disclosure of Invention
The embodiment of the invention aims to provide a synthetic method of 2-chloro-5-chloromethyl thiazole, aiming at solving the problems in the background art.
The embodiment of the invention is realized by a method for synthesizing 2-chloro-5-chloromethyl thiazole, which comprises the following steps:
placing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent for mixing to obtain a mixed solution;
adding an oxidant into the mixed solution for reaction to obtain a reaction solution;
standing and layering the reaction solution to obtain an organic layer;
and (3) cleaning the organic layer, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
In a preferable embodiment of the present invention, in the step, the mass ratio of 1-isothiocyanato-2-chloro-2-propene to the organic solvent is 1 (0-6).
As another preferable mode of the embodiment of the present invention, the organic solvent is any one of chloroform, 1, 2-dichloroethane, dichloromethane, toluene, benzene, methyl t-butyl ether, and the like.
In another preferable embodiment of the present invention, in the step, a reaction temperature of adding an oxidizing agent to the mixed solution for reaction is controlled to be 0 to 70 ℃.
In another preferred embodiment of the present invention, the oxidizing agent is any one of hydrogen peroxide, sodium hypochlorite, calcium hypochlorite, ozone, potassium permanganate, sodium chlorate, and the like.
In another preferable embodiment of the invention, in the step, the reaction temperature of adding the oxidant into the mixed solution for reaction is controlled to be 15-35 ℃.
As another preferable scheme of the embodiment of the invention, the mass concentration of the hydrochloric acid is 15-38%.
As another preferable embodiment of the present invention, the step of mixing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent to obtain a mixed solution specifically includes:
1-isothiocyanato-2-chloro-2-propene, hydrochloric acid and an inorganic chloride are mixed in water and/or an organic solvent to obtain a mixed solution. Wherein the inorganic chloride is calcium chloride, sodium chloride, potassium chloride, ammonium chloride, etc.
The synthesis method of 2-chloro-5-chloromethyl thiazole provided by the embodiment of the invention simplifies the reaction steps, the waste water after the reaction has weak acidity, the waste water only needs slightly adjusting alkali, the salt content is low, the treatment is easy, meanwhile, the hydrochloric acid is also a relatively abundant raw material in the market and is easy to obtain, the highly toxic chlorine is not suitable for the reaction process, the reaction is carried out in time after trace chlorine is generated on site through the reaction system, and the hidden trouble of chlorine leakage does not exist.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene and a proper amount of hydrochloric acid with the mass concentration of 38% into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein, the addition amount of the hydrochloric acid can be determined according to the content of chlorine element needed by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 25 ℃ to obtain a reaction solution. Wherein the oxidant is hydrogen peroxide, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 2
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing a proper amount of hydrochloric acid with the mass concentration of 15% and calcium chloride with the same mass into a reaction bottle, stirring, adding 100g of 1-isothiocyanato-2-chloro-2-propylene into the reaction bottle, stirring and mixing to obtain a mixed solution. Wherein, the addition amount of the hydrochloric acid can be determined according to the content of chlorine element needed by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 25 ℃ to obtain a reaction solution. Wherein the oxidant is hydrogen peroxide, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 1h, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 3
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing a proper amount of hydrochloric acid with the mass concentration of 15% and calcium chloride with the same mass into a reaction bottle, stirring, adding 100g of 1-isothiocyanato-2-chloro-2-propylene into the reaction bottle, stirring and mixing to obtain a mixed solution. Wherein, the addition amount of the hydrochloric acid can be determined according to the content of chlorine element needed by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 30 ℃ to obtain a reaction solution. Wherein, the oxidant is potassium permanganate solution, and the addition amount of the oxidant can completely oxidize hydrochloric acid into chlorine;
s3, stirring the reaction solution for 1h, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 4
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 38% and 300g of organic solvent into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is dichloromethane; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
and S2, introducing a proper amount of oxidant into the mixed solution to react, and controlling the reaction temperature to be 25 ℃ to obtain a reaction solution. Wherein the oxidant is ozone, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 5
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 15% and 600g of organic solvent into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is chloroform; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 0 ℃ to obtain a reaction solution. Wherein, the oxidant is calcium hypochlorite solution, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 1h, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 6
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 36% and 100g of organic solvent into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is 1, 2-dichloroethane; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 70 ℃ to obtain a reaction solution. Wherein, the oxidant is sodium chlorate solution, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 7
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 20% and 400g of organic solvent into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is dichloromethane; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 15 ℃ to obtain a reaction solution. Wherein the oxidant is hydrogen peroxide, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 8
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 25% and 300g of organic solvent into a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is toluene; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 35 ℃ to obtain a reaction solution. Wherein the oxidant is hydrogen peroxide, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 9
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propene, an appropriate amount of hydrochloric acid with the mass concentration of 36%, 100g of water and 100g of organic solvent in a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein the organic solvent is chloroform; the addition amount of the hydrochloric acid can be determined according to the content of chlorine element required by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 50 ℃ to obtain a reaction solution. Wherein the oxidant is hydrogen peroxide, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
Example 10
This example provides a method for the synthesis of 2-chloro-5-chloromethylthiazole, comprising the steps of:
s1, placing 100g of 1-isothiocyanato-2-chloro-2-propylene, a proper amount of hydrochloric acid with the mass concentration of 38% and 100g of water in a reaction bottle, and stirring and mixing to obtain a mixed solution. Wherein, the addition amount of the hydrochloric acid can be determined according to the content of chlorine element needed by the 1-isothiocyanato-2-chloro-2-propene;
s2, adding a proper amount of oxidant into the mixed solution for reaction, and controlling the reaction temperature to be 40 ℃ to obtain a reaction solution. Wherein, the oxidant is sodium hypochlorite solution, and the addition amount of the oxidant is enough to oxidize all hydrochloric acid into chlorine;
s3, stirring the reaction solution for 2 hours, and then standing for layering to obtain an organic layer;
s4, washing the organic layer once with water, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
The contents and yields of the 2-chloro-5-chloromethylthiazole synthesized in examples 1 to 4 were measured, and the measurement results are shown in table 1.
TABLE 1
| Synthesis method | Product content | Yield of product |
| Example 1 | 98.5% | 93% |
| Example 2 | 98.2% | 95% |
| Example 3 | 98.2% | 95% |
| Example 4 | 97.5% | 83% |
In conclusion, the synthesis method provided by the embodiment of the invention simplifies the reaction steps, the wastewater after the reaction has weak acidity, the wastewater only needs slightly adjusted alkali, the salt content is low, the wastewater is easy to treat, meanwhile, the hydrochloric acid is a relatively abundant raw material in the market and is easy to obtain, the highly toxic chlorine is not suitable for the reaction process, the reaction is carried out in time after trace chlorine is generated on site through a reaction system, the hidden danger of chlorine leakage does not exist, and the obtained product has high purity and high yield.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (8)
1. A synthetic method of 2-chloro-5-chloromethyl thiazole is characterized by comprising the following steps:
placing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent for mixing to obtain a mixed solution;
adding an oxidant into the mixed solution for reaction to obtain a reaction solution;
standing and layering the reaction solution to obtain an organic layer;
and (3) cleaning the organic layer, and then distilling under reduced pressure to obtain the 2-chloro-5-chloromethyl thiazole.
2. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein the mass ratio of 1-isothiocyanato-2-chloro-2-propene to the organic solvent in the step is 1 (0-6).
3. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1 or 2, wherein the organic solvent is any one of chloroform, 1, 2-dichloroethane, dichloromethane, toluene, benzene, methyl tert-butyl ether.
4. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein the reaction temperature of the reaction mixture is controlled to be 0-70 ℃ by adding an oxidant.
5. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1 or 4, wherein the oxidant is any one of hydrogen peroxide, sodium hypochlorite, calcium hypochlorite, ozone, potassium permanganate and sodium chlorate.
6. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 4, wherein the reaction temperature of the step of adding oxidant into the mixture is controlled to be 15-35 ℃.
7. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein the mass concentration of hydrochloric acid is 15-38%.
8. The method for synthesizing 2-chloro-5-chloromethylthiazole as claimed in claim 1, wherein the step of mixing 1-isothiocyanato-2-chloro-2-propene and hydrochloric acid in water and/or an organic solvent to obtain a mixture comprises:
1-isothiocyanato-2-chloro-2-propene, hydrochloric acid and an inorganic chloride are mixed in water and/or an organic solvent to obtain a mixed solution.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754609A (en) * | 2021-10-11 | 2021-12-07 | 邯郸市瑞田农药有限公司 | 2-chloro-5-chloromethyl thiazole prepared by aqueous phase method and synthesis process thereof |
| CN116102517A (en) * | 2022-11-14 | 2023-05-12 | 郑州大学 | Synthesis method of 2-chloro-5-chloromethylthiazole |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
| CN105254584A (en) * | 2015-11-20 | 2016-01-20 | 河北德瑞化工有限公司 | Preparation method of 2-chloro-5-chloromethyl thiazole |
| CN105949145A (en) * | 2016-06-03 | 2016-09-21 | 江西邦浦医药化工有限公司 | Green synthesis method for high-quality 2-chloro-5-chloromethylthiazole |
| CN109293596A (en) * | 2018-09-30 | 2019-02-01 | 江苏润泽鑫生物科技有限公司 | The preparation method of 2- chloro-5-chloromethyl thiazole |
| CN111170930A (en) * | 2018-11-12 | 2020-05-19 | 新发药业有限公司 | Simple preparation method of 5, 6-dihydropyridine-2 (1H) -ketone derivative |
-
2020
- 2020-09-17 CN CN202010981058.4A patent/CN112409289A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
| CN105254584A (en) * | 2015-11-20 | 2016-01-20 | 河北德瑞化工有限公司 | Preparation method of 2-chloro-5-chloromethyl thiazole |
| CN105949145A (en) * | 2016-06-03 | 2016-09-21 | 江西邦浦医药化工有限公司 | Green synthesis method for high-quality 2-chloro-5-chloromethylthiazole |
| CN109293596A (en) * | 2018-09-30 | 2019-02-01 | 江苏润泽鑫生物科技有限公司 | The preparation method of 2- chloro-5-chloromethyl thiazole |
| CN111170930A (en) * | 2018-11-12 | 2020-05-19 | 新发药业有限公司 | Simple preparation method of 5, 6-dihydropyridine-2 (1H) -ketone derivative |
Non-Patent Citations (3)
| Title |
|---|
| 毛春晖等: "2-氯-5-氯甲基-1,3-噻唑的合成方法", 《精细化工中间体》 * |
| 秦浩正: "《中学生学习辞典 化学卷》", 30 September 2012, 上海世界图书出版公司 * |
| 黄金艳: "2-氯-5-氯甲基-1,3-噻唑的合成", 《河北化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113754609A (en) * | 2021-10-11 | 2021-12-07 | 邯郸市瑞田农药有限公司 | 2-chloro-5-chloromethyl thiazole prepared by aqueous phase method and synthesis process thereof |
| CN116102517A (en) * | 2022-11-14 | 2023-05-12 | 郑州大学 | Synthesis method of 2-chloro-5-chloromethylthiazole |
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