CN109535036B - Synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate - Google Patents
Synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate Download PDFInfo
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Abstract
The invention discloses a synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, relating to the field of pesticide preparation; adopts a process route that p-trifluoromethoxyaniline firstly reacts with methyl chloroformate after acylation with phosgene: at low temperature, p-trifluoromethoxybenzene reacts with phosgene to obtain p-trifluoromethoxyphenyl carbamyl chloride; the method comprises the steps of reacting p-trifluoromethoxyphenyl carbamoyl chloride with methyl chloroformate to obtain methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, wherein phosgene can directly react with p-trifluoromethoxyaniline without a catalyst, so that the steps of water cutting before reaction, water washing after reaction and the like in the prior art are omitted, the flow of phosgene introduced into a reaction system can be controlled, the reaction process is controlled, the use of strong corrosive sodium cyanide or mixed alkali with poor stability in the prior art as an initiator is avoided, the operation steps are simplified, the reaction period is shortened, the production cost is reduced, and the method is easier to industrialize.
Description
Technical Field
The invention discloses a synthetic method, relates to the field of pesticide preparation, and particularly relates to a synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate.
Background
Indoxacarb (C)22H17ClF3N3O7The common name indoxacarb) is a novel efficient and low-toxicity oxadiazine sodium channel blocker type pesticide developed by DuPont in the last century, has wide insecticidal spectrum and quick response, has excellent control effect on resistant pests such as beet armyworm, diamond back moth, cotton bollworm and the like, has no cross resistance with other pesticides, and has no carcinogenic, teratogenic and mutagenic effects. Indoxacarb is one of the alternative varieties for replacing high-toxicity and high-residue pesticides which are demonstrated and popularized in large area in the department of agriculture in China.
Methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate is one of the important intermediates for synthesizing indoxacarb, and is in a white crystal shape. The existing synthesis technology mostly adopts a process route that p-trifluoromethoxyaniline is firstly substituted with methyl chloroformate and then reacts with solid phosgene or diphosgene, and mainly comprises the steps of dropwise adding an alkali solution into a mixed solution of p-trifluoromethoxyaniline, methyl chloroformate and toluene to prepare 4- (trifluoromethoxy) phenyl methyl carbamate, and then dropwise adding slurry obtained by fully mixing 4- (trifluoromethoxy) phenyl methyl carbamate and initiators such as sodium cyanide or mixed alkali into triphosgene or diphosgene, or dropwise adding a phosgene toluene solution into the slurry to prepare chloroformyl [4- (trifluoromethoxy) phenyl ] methyl carbamate. However, in the existing process, no matter the slurry is dripped into triphosgene or diphosgene, or the toluene solution of phosgene is dripped into the slurry, the dripping speed is very slow, otherwise, phosgene is easy to overflow in large quantity, so that the risk is high, and the two-step reaction requires post-treatment steps such as water washing, layering and the like, so that more waste water is generated, and the reaction period is long. The invention provides a synthesis method of methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, which adopts a process route that p-trifluoromethoxyaniline firstly reacts with methyl chloroformate after acylation with phosgene: at low temperature, p-trifluoromethoxybenzene reacts with phosgene to obtain p-trifluoromethoxyphenyl carbamyl chloride; the method comprises the steps of reacting p-trifluoromethoxyphenyl carbamoyl chloride with methyl chloroformate to obtain methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, wherein phosgene can directly react with p-trifluoromethoxyaniline without a catalyst, so that the steps of water cutting before reaction, water washing after reaction and the like in the prior art are omitted, the flow of phosgene introduced into a reaction system can be controlled, the reaction process is controlled, and meanwhile, the use of strong corrosive sodium cyanide or mixed alkali with poor stability in the prior art as an initiator is avoided, so that the operation steps are simplified, the reaction period is shortened, the production cost is reduced, and the method is easier to industrialize.
Disclosure of Invention
The invention provides a synthetic method of methyl indoxacarb intermediate chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate aiming at the problems in the prior art.
The specific scheme provided by the invention is as follows:
a synthetic method of methyl indoxacarb intermediate chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate comprises the following specific steps:
step 1: introducing phosgene into a toluene solution at the temperature of between 5 ℃ below zero and 5 ℃, then dropwise adding a toluene solution of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution, removing redundant gas,
step 2: adding an acid-binding agent into the reaction solution, dropwise adding methyl chloroformate at-10-10 deg.C, controlling the temperature of the reaction solution not to exceed 15 deg.C for reaction, keeping the temperature of the reaction solution after reaction,
and step 3: and (3) after the reaction solution is kept warm, washing, concentrating, crystallizing and drying to obtain a white solid product.
In the step 1 of the synthesis method, phosgene is introduced into a toluene solution at the temperature of-5-5 ℃ for 0.25-1.5h, a toluene solution of p-trifluoromethoxyaniline is dropwise added for 1-3h, and the reaction solution is kept warm and then redundant gas is removed.
In the step 1 of the synthesis method, after the toluene solution of the p-trifluoromethoxyaniline is dropwise added, the temperature of the reaction solution is kept at 0-15 ℃, and the temperature is kept for 1-2 h.
In the step 2 of the synthesis method, the temperature of the reaction solution is reduced to-10-10 ℃, an acid-binding agent is added, and the temperature difference between the reaction solution before dropping and the methyl chloroformate dropping process is controlled not to exceed 10 ℃.
Adding an acid-binding agent into the reaction liquid in the step 2 of the synthesis method, dropwise adding methyl chloroformate at the temperature of-10-10 ℃ for 1-3h, controlling the temperature of the reaction liquid not to exceed 15 ℃ for reaction, and preserving the temperature of the reaction liquid for 1.5-3.5h after the reaction.
The acid-binding agent in step 2 of the synthesis method is one or a mixture of more of triethylamine, pyridine, N-diisopropylethylamine, 4-dimethylaminopyridine, triethanolamine, tetrabutylammonium bromide, potassium carbonate, ammonium carbonate and sodium carbonate.
An indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate is prepared according to the following steps:
step 1: introducing phosgene into a toluene solution at the temperature of between 5 ℃ below zero and 5 ℃, then dropwise adding a toluene solution of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution, removing redundant gas,
step 2: adding an acid-binding agent into the reaction solution, dropwise adding methyl chloroformate at-10-10 deg.C, controlling the temperature of the reaction solution not to exceed 15 deg.C for reaction, keeping the temperature of the reaction solution after reaction,
and step 3: and (3) after the reaction solution is kept warm, washing, concentrating, crystallizing and drying to obtain a white solid product.
The indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate is prepared by the steps of finishing dropping a toluene solution of p-trifluoromethoxyaniline in the step 1, keeping the temperature of a reaction solution at 0-15 ℃, and preserving heat for 1-2 hours.
In the preparation step 2 of the indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, the temperature of a reaction solution is reduced to-10-10 ℃, an acid-binding agent is added, and the temperature difference between the reaction solution before dropping and the methyl chloroformate dropping process is controlled not to exceed 10 ℃.
In the preparation step 2 of the indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, an acid-binding agent is added into reaction liquid, methyl chloroformate at the temperature of-10-10 ℃ is dropwise added for 1-3h, the temperature of the reaction liquid is controlled not to exceed 15 ℃ for reaction, and the reaction liquid is kept warm for 1.5-3.5h after the reaction.
The invention has the advantages that:
the invention provides a synthesis method of methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, which adopts a process route that p-trifluoromethoxyaniline firstly reacts with methyl chloroformate after acylation with phosgene: at low temperature, p-trifluoromethoxybenzene reacts with phosgene to obtain p-trifluoromethoxyphenyl carbamyl chloride; the method comprises the steps of reacting p-trifluoromethoxyphenyl carbamoyl chloride with methyl chloroformate to obtain methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, wherein phosgene can directly react with p-trifluoromethoxyaniline without a catalyst, so that the steps of water cutting before reaction, water washing after reaction and the like in the prior art are omitted, the flow of phosgene introduced into a reaction system can be controlled, the reaction process is controlled, and meanwhile, the use of strong corrosive sodium cyanide or mixed alkali with poor stability in the prior art as an initiator is avoided, so that the operation steps are simplified, the reaction period is shortened, the production cost is reduced, and the method is easier to industrialize; and the yield of the product is more than 93 percent, and the purity reaches more than 96 percent.
Drawings
FIG. 1 is a schematic of a synthetic scheme of the present invention;
FIG. 2 is a schematic flow diagram of the process of the present invention.
Detailed Description
The invention provides a method for synthesizing an indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate, which comprises the following specific steps:
step 1: introducing phosgene into a toluene solution at the temperature of between 5 ℃ below zero and 5 ℃, then dropwise adding a toluene solution of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution, removing redundant gas,
step 2: adding an acid-binding agent into the reaction solution, dropwise adding methyl chloroformate at-10-10 deg.C, controlling the temperature of the reaction solution not to exceed 15 deg.C for reaction, keeping the temperature of the reaction solution after reaction,
and step 3: and (3) after the reaction solution is kept warm, washing, concentrating, crystallizing and drying to obtain a white solid product.
Meanwhile, the indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate is prepared by the synthesis method.
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Example 1
Step 1: putting a proper amount of toluene into a 500ml reaction bottle, cooling to-5-0 ℃, introducing phosgene into the solution, and generating the phosgene according to a conventional method, wherein the mass content is as follows: COCl2 91.9％，Cl2 0.13％，CO2 3.01％，CO 3.96％，N2 0.6％，O20.1 percent of the total content of the impurities, 0.3 percent of the total content of the impurities,
introducing phosgene for 0.25h, dropwise adding a toluene solution containing 0.3mol of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution at 0-5 ℃ after 1h of dropwise adding, preserving the temperature for 1h,
after the heat preservation is finished, keeping the temperature of the reaction liquid, and introducing nitrogen to expel excess phosgene and generated hydrogen chloride;
step 2: cooling the obtained reaction liquid to-10 to-5 ℃, adding 0.6mol of triethylamine, dropwise adding 0.33mol of methyl chloroformate for 1h, keeping the temperature of the reaction liquid not to exceed 0 ℃ in the dropwise adding process,
keeping the temperature of the reaction solution for 1.5h after the reaction;
and step 3: after the heat preservation is finished, washing with water at normal temperature, adjusting the water consumption according to the generated salt and whether the salt is recycled,
vacuum distillation and concentration are carried out under the pressure of about-0.08 MPa, most of solvent toluene is removed,
cooling to about 10 ℃ after concentration, basically separating out product crystals, filtering,
and drying the filtered solid product to obtain a white solid product with the content of 95.5 percent and the yield of 93.4 percent.
Example 2
Step 1: putting a proper amount of toluene into a 500ml reaction bottle, cooling to-5-0 ℃, introducing phosgene into the solution, and generating the phosgene according to a conventional method, wherein the mass content is as follows: COCl2 92.9％，Cl2 0.13％，CO2 2.01％，CO 3.56％，N2 0.8％，O20.3% and 0% impurity.3％，
Introducing phosgene for 0.5h, dropwise adding a toluene solution containing 0.3mol of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution at 3-8 ℃ after finishing dropwise adding for 1.5h, preserving the temperature for 1.5h,
after the heat preservation is finished, keeping the temperature of the reaction liquid, and introducing nitrogen to expel excess phosgene and generated hydrogen chloride;
step 2: cooling the obtained reaction liquid to-5-0 ℃, adding 0.65mol of N, N-diisopropylethylamine and triethylamine, dropwise adding 0.37mol of methyl chloroformate for 1.5h, keeping the temperature of the reaction liquid not more than 5 ℃ in the dropwise adding process, and preserving the temperature of the reaction liquid for 2h after reaction;
and step 3: after the heat preservation is finished, washing with water at normal temperature, adjusting the water consumption according to the generated salt and whether the salt is recycled,
vacuum distillation and concentration are carried out under the pressure of about-0.08 MPa, most of solvent toluene is removed,
cooling to about 10 ℃ after concentration, basically separating out product crystals, filtering,
and drying the filtered solid product to obtain a white solid product with the content of 95.8 percent and the yield of 93.7 percent.
Example 3
Step 1: putting a proper amount of toluene into a 500ml reaction bottle, cooling to 3-8 ℃, introducing phosgene into the solution, and generating the phosgene according to a conventional method, wherein the mass content is as follows: COCl2 91.7％，Cl2 0.14％，CO2 2.91％，CO 3.06％，N21％，O20.6 percent of the total weight of the mixture, 0.3 percent of impurities,
introducing phosgene for 0.75h, dropwise adding a toluene solution containing 0.3mol of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution at 5-10 ℃ after 2h of dropwise adding, preserving the temperature for 2h,
after the heat preservation is finished, keeping the temperature of the reaction liquid, and introducing nitrogen to expel excess phosgene and generated hydrogen chloride;
step 2: cooling the obtained reaction liquid to 0-5 ℃, adding 0.7mol of triethylamine and ammonium carbonate, dripping 0.43mol of methyl chloroformate for 2h, keeping the temperature of the reaction liquid not to exceed 5 ℃ in the dripping process,
keeping the temperature of the reaction solution for 2.5h after the reaction;
and step 3: after the heat preservation is finished, washing with water at normal temperature, adjusting the water consumption according to the generated salt and whether the salt is recycled,
vacuum distillation and concentration are carried out under the pressure of about-0.08 MPa, most of solvent toluene is removed,
cooling to about 10 ℃ after concentration, basically separating out product crystals, filtering,
and drying the filtered solid product to obtain a white solid product with the content of 96.2 percent and the yield of 93.1 percent.
Example 4
Step 1: putting a proper amount of toluene into a 500ml reaction bottle, cooling to 5-8 ℃, introducing phosgene into the solution, and generating the phosgene according to a conventional method, wherein the mass content is as follows: COCl2 92.5％，Cl2 0.14％，CO2 2.51％，CO 3.06％，N20.7％，O20.5 percent of the total weight of the mixture, 0.3 percent of impurities,
after phosgene is introduced for 1h, a toluene solution containing 0.3mol of p-trifluoromethoxyaniline is dripped, after the dripping is finished for 2.5h, the temperature of the reaction solution is kept at 7-12 ℃, the temperature is kept for 2h,
after the heat preservation is finished, keeping the temperature of the reaction liquid, and introducing nitrogen to expel excess phosgene and generated hydrogen chloride;
step 2: cooling the obtained reaction liquid to 5-10 ℃, adding 0.8mol of N, N-diisopropylethylamine and triethanolamine, dripping 0.5mol of methyl chloroformate for 2.5h, keeping the temperature of the reaction liquid not to exceed 15 ℃ in the dripping process,
keeping the temperature of the reaction solution for 3 hours after the reaction;
and step 3: after the heat preservation is finished, washing with water at normal temperature, adjusting the water consumption according to the generated salt and whether the salt is recycled,
vacuum distillation and concentration are carried out under the pressure of about-0.08 MPa, most of solvent toluene is removed,
cooling to about 10 ℃ after concentration, basically separating out product crystals, filtering,
and drying the filtered solid product to obtain a white solid product with the content of 96.3 percent and the yield of 93.6 percent.
Example 5
Step 1: adding proper amount of toluene into 500ml of tolueneCooling to 7-10 ℃ in a bottle, introducing phosgene into the solution, and generating the phosgene according to a conventional method, wherein the mass content is as follows: COCl2 92.7％，Cl2 0.14％，CO2 2.91％，CO 2.56％，N2 1.3％，O20.8 percent and 0.3 percent of impurities,
introducing phosgene for 1.5h, dropwise adding a toluene solution containing 0.3mol of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution at 10-15 ℃ after the dropwise adding is finished for 3h, preserving the temperature for 2.5h,
after the heat preservation is finished, keeping the temperature of the reaction liquid, and introducing nitrogen to expel excess phosgene and generated hydrogen chloride;
step 2: cooling the obtained reaction liquid to 5-10 ℃, adding 0.85mol of triethanolamine, dripping 0.55mol of methyl chloroformate for 3h, keeping the temperature of the reaction liquid not to exceed 15 ℃ in the dripping process,
keeping the temperature of the reaction solution for 3.5h after the reaction;
and step 3: after the heat preservation is finished, washing with water at normal temperature, adjusting the water consumption according to the generated salt and whether the salt is recycled,
vacuum distillation and concentration are carried out under the pressure of about-0.08 MPa, most of solvent toluene is removed,
cooling to about 10 ℃ after concentration, basically separating out product crystals, filtering,
and drying the filtered solid product to obtain a white solid product with the content of 96.3 percent and the yield of 93.6 percent.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (6)
1. A synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate is characterized by comprising the following specific steps:
step 1: introducing phosgene into a toluene solution at the temperature of between 5 ℃ below zero and 5 ℃, then dropwise adding a toluene solution of p-trifluoromethoxyaniline, keeping the temperature of the reaction solution, removing redundant gas,
step 2: adding an acid-binding agent into the reaction solution, dropwise adding methyl chloroformate at-10-10 deg.C, controlling the temperature of the reaction solution not to exceed 15 deg.C for reaction, keeping the temperature of the reaction solution after reaction,
and step 3: and (3) after the reaction solution is kept warm, washing, concentrating, crystallizing and drying to obtain a white solid product.
2. The synthesis process of claim 1, wherein in step 1 phosgene is introduced into toluene solution at-5-5 deg.c for 0.25-1.5 hr, p-trifluoromethoxyaniline solution is dropped for 1-3 hr, and the reaction liquid is maintained for heat preservation before eliminating excessive gas.
3. The synthesis method according to claim 1 or 2, wherein the temperature of the reaction solution is kept at 0-15 ℃ for 1-2h after the dropwise addition of the p-trifluoromethoxyaniline in toluene in step 1.
4. A synthesis method according to claim 3, characterized in that in step 2, the temperature of the reaction solution is reduced to-10-10 ℃, an acid-binding agent is added, and the temperature difference between the reaction solution before the dropwise addition and the methyl chloroformate dropwise addition is controlled not to exceed 10 ℃.
5. The synthesis method of claim 1 or 4, wherein in the step 2, an acid-binding agent is added into the reaction solution, methyl chloroformate at-10-10 ℃ is dropwise added for 1-3h, the temperature of the reaction solution is controlled not to exceed 15 ℃ for reaction, and the reaction solution is kept warm for 1.5-3.5h after the reaction.
6. The synthesis method of claim 5, wherein the acid binding agent in step 2 is one or more of triethylamine, pyridine, N-diisopropylethylamine, 4-dimethylaminopyridine, triethanolamine, tetrabutylammonium bromide, potassium carbonate, ammonium carbonate and sodium carbonate.
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