CN107986991A - The synthetic method of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate - Google Patents
The synthetic method of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate Download PDFInfo
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- CN107986991A CN107986991A CN201711362249.7A CN201711362249A CN107986991A CN 107986991 A CN107986991 A CN 107986991A CN 201711362249 A CN201711362249 A CN 201711362249A CN 107986991 A CN107986991 A CN 107986991A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
Abstract
The application provides a kind of synthetic method of N chloroformyls N [(4 trifluoromethoxy) phenyl] methyl carbamate; 4 trifluoro-methoxyanilines for being dissolved in toluene and methylchloroformate can be generated N [(4 trifluoromethoxy) phenyl] methyl carbamate by this method in 50 ~ 110 DEG C of reactions; acid binding agent need not be added; the generation of side reaction can be effectively reduced, subsequent product quality is preferable.In addition, using sodium tert-butoxide or potassium tert-butoxide as activation base reagent in above-mentioned synthetic method, avoid laboring choline reagent using the very high sodium hydrogen of reactivity, make production process safer, significantly reduce accident rate.
Description
Technical field
The present invention relates to chloride compounds technical field, more particularly to N- chloroformyls-N [(4- trifluoromethoxies) benzene
Base] methyl carbamate synthetic method.
Background technology
Indoxacarb（indoxacarb）It is a kind of ammonia containing oxadiazines structure of the du pont company in exploitation in 1992
Carbamate insecticides, chemical name are chloro- 2,3,4a, the 5- tetrahydrochysenes -2 of (4aS) -7- { methoxycarbonyl [(4- trifluoro methoxies
Base) phenyl] carbamoyl } indeno [1,2-e] [1,3,4-] oxadiazines -4a- carboxylate methyl esters.It is a chiral molecules, because
It is efficiently, low toxicity, low-residual, insecticidal spectrum are wide and are subject to the weight of global pesticide industry without the characteristics of carcinogenic teratogenesis mutagenesis
Depending on.Its mechanism of action is the sodium-ion channel blocked in pest nerve cell, causes target pest ataxia, paralysis, no
Final death can be fed, so as to protect Target crops well.
N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is the key intermediate for synthesizing indoxacarb
One of.The synthetic method of traditional N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is with 4- fluoroforms
Epoxide aniline is raw material, and acid binding agent is done with sodium carbonate, sodium acid carbonate or triethylamine etc., reacts generation N- [(4- with methylchloroformate
Trifluoromethoxy) phenyl] methyl carbamate, then choline reagent is labored into salt with sodium hydrogen, sodium salt and phosgene, surpalite or three light
Solid/liquid/gas reactions obtain target product.Since this method adds acid binding agent, side reaction can be caused, seriously affect product quality.
The content of the invention
Based on this, it is necessary to provide a kind of conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate
Into method, this method need not add acid binding agent, can effectively reduce the generation of side reaction, and obtained product quality is preferable.
A kind of synthetic method of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate, including following step
Suddenly：
4- trifluoro-methoxyanilines are dissolved in toluene, are warming up to 50 DEG C ~ 110 DEG C, methylchloroformate, insulation reaction 1 ~ 5 is added dropwise
Hour, washing, reflux water-dividing obtains the reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate to anhydrous；
Activation base reagent, heating are added into the reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
To 100 DEG C ~ 110 DEG C removing tert-butyl alcohols, the reaction solution containing sodium salt is obtained；
At 0 DEG C ~ 10 DEG C, phosgene is passed through into toluene, adds pyridine, the reaction solution containing sodium salt, insulation reaction 0.5 is added dropwise
~ 1.5 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate；
The reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is concentrated,
Freezing and crystallizing, filtering, drying, obtain the N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
In one of the embodiments, the activation base reagent is sodium tert-butoxide or potassium tert-butoxide.
In one of the embodiments, the molar ratio of the 4- trifluoro-methoxyanilines and the methylchloroformate is：1：1
~1.5。
In one of the embodiments, the molar ratio of the 4- trifluoro-methoxyanilines and the activation base reagent is：1：1
~1.5。
In one of the embodiments, the mass ratio of the phosgene and pyridine is：100：4~6.
In one of the embodiments, the condition of the concentration is：Temperature be 78 DEG C ~ 82 DEG C, vacuum for -0.09MPa ~
0.095MPa。
In one of the embodiments, the temperature of the freezing and crystallizing is -2 DEG C ~ 2 DEG C.
In one of the embodiments, the condition of the drying is：Temperature is 55 DEG C ~ 65 DEG C, when the time is 22 ~ 26 small.
The synthetic method of above-mentioned N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate, will be dissolved in toluene
4- trifluoro-methoxyanilines and methylchloroformate can generate N- [(4- trifluoromethoxies) phenyl] ammonia in 50 ~ 110 DEG C of reactions
Base methyl formate, the step need not add acid binding agent, can effectively reduce the generation of side reaction, and subsequent product quality is preferable.
In addition, in above-mentioned synthetic method, using sodium tert-butoxide or potassium tert-butoxide as activation base reagent, avoid using reaction
The very high sodium hydrogen of activity is labored choline reagent, is made production process safer, is significantly reduced accident rate.
Embodiment
For the ease of understand the present invention, the present invention will be described more fully below, and give the present invention compared with
Good embodiment.But the present invention can realize in many different forms, however it is not limited to embodiment described herein.Phase
Instead, there is provided the purpose of these embodiments is the understanding more thorough and comprehensive made to the disclosure.
Unless otherwise defined, all of technologies and scientific terms used here by the article is with belonging to technical field of the invention
The normally understood implication of technical staff is identical.Term used in the description of the invention herein is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term as used herein "and/or" includes one or more phases
The arbitrary and all combination of the Listed Items of pass.
The synthetic method of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate of one embodiment, bag
Include following steps S110 ~ S140：
4- trifluoro-methoxyanilines, be dissolved in toluene by S110, is warming up to 50 DEG C ~ 110 DEG C, and methylchloroformate is added dropwise, and insulation is anti-
Answer 1 ~ 5 it is small when, washing, reflux water-dividing is obtained containing the anti-of N- [(4- trifluoromethoxies) phenyl] methyl carbamate to anhydrous
Answer liquid.
Wherein, the molar ratio of 4- trifluoro-methoxyanilines and methylchloroformate is 1:1~1.5.
Preferably, the temperature of insulation reaction is 78 DEG C ~ 82 DEG C.
The step need not add acid binding agent, by controlling reaction temperature at 50 DEG C ~ 110 DEG C so that react the chlorination of generation
Hydrogenization is overflowed, and reaction is able to smoothly carry out to positive reaction direction, effectively reduces the generation of side reaction, subsequent product quality compared with
It is good.
4- trifluoro-methoxyanilines and the methylchloroformate reaction of toluene will be dissolved in, generate N- [(4- trifluoromethoxies) benzene
Base] methyl carbamate and hydrogen chloride, hydrogen chloride gasification is overflowed to be absorbed using lye, prevents from entering air pollution environmental, excessively
Methylchloroformate then removed by washing, and since water can destroy the activity of activation base reagent, which need to flow back point
Water is to anhydrous.
Also contain toluene in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate.
S120, add activation alkali into the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Reagent, is warming up to 100 DEG C ~ 110 DEG C removing tert-butyl alcohols, obtains the reaction solution containing sodium salt.
Wherein, the molar ratio of 4- trifluoro-methoxyanilines and activation base reagent is 1:1~1.5.
It is sodium tert-butoxide or potassium tert-butoxide to activate base reagent.
Step S120, as activation base reagent, is avoided using the higher sodium of reactivity using sodium tert-butoxide or potassium tert-butoxide
Hydrogen, in process of production safe coefficient higher.
Also contain toluene in the above-mentioned reaction solution containing sodium salt.
S130, at 0 DEG C ~ 10 DEG C, be passed through phosgene into toluene, add pyridine, the above-mentioned reaction solution 4 ~ 6 containing sodium salt is added dropwise
Hour, drip rear insulation reaction 0.5 ~ 1.5 it is small when, obtain containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] amino
The reaction solution of methyl formate.
Wherein, the mass ratio of phosgene and pyridine is 100:4~6.
Also contain in the above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate
Toluene.
S140, by the above-mentioned reaction solution water containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate
Wash, concentrate, freezing and crystallizing, filtering, drying, obtain N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
Wherein, the condition of concentration is：Temperature is 78 DEG C ~ 82 DEG C, and vacuum is -0.09MPa ~ 0.095MPa.
The temperature of freezing and crystallizing is -2 DEG C ~ 2 DEG C.
Dry condition is：Temperature is 55 DEG C ~ 65 DEG C, when the time is 22 ~ 26 small.
It should be noted that the separation of above-mentioned N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate carries
Pure method is not limited to washing described above, concentration, freezing and crystallizing, filtering, drying process, other can be from containing N- chloroformyls
N- chloroformyls-N [(4- trifluoromethoxies) is obtained in the reaction solution of base-N [(4- trifluoromethoxies) phenyl] methyl carbamate
Phenyl] method of methyl carbamate can also.
Above-mentioned steps S110 ~ S140（By taking sodium tert-butoxide as an example）Reaction equation it is as follows：
N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate synthesized by step S110 ~ S140, purity
More than 96%.
The synthetic method of above-mentioned N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate, will be dissolved in toluene
4- trifluoro-methoxyanilines and methylchloroformate can generate N- [(4- trifluoromethoxies) phenyl] ammonia in 50 ~ 110 DEG C of reactions
Base methyl formate, the step need not add acid binding agent, can effectively reduce the generation of side reaction, and subsequent product quality is preferable.
In addition, in above-mentioned synthetic method, using sodium tert-butoxide or potassium tert-butoxide as activation base reagent, avoid using reaction
The very high sodium hydrogen of activity is labored choline reagent, is made production process safer, is significantly reduced accident rate.
N- chloroformyls-N [(4- trifluoromethoxies) phenyl] the methyl carbamate purity produced is more than 96%.
It is specific embodiment below
Embodiment 1
By 17.88g 4- trifluoro-methoxyanilines（99%, 0.10mol）It is dissolved in 100g toluene, is warming up to 80 DEG C of dropwise addition chloro-carbonic acids
Methyl esters 11.45g（99%, 0.12mol）, when insulation reaction 3 is small, washing, reflux water-dividing is obtained containing N- [(4- trifluoros to anhydrous
Methoxyl group) phenyl] methyl carbamate reaction solution.
Sampling detects, N- [(4- tri- in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Fluorine methoxyl group) phenyl] methyl carbamate mass content be 98.5%, moisture 0.08%.
The 9.8g tert-butyl alcohols are added into the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Sodium（98%, 0.10mol）, 110 DEG C of removing tert-butyl alcohols are warming up to, obtain the reaction solution containing sodium salt.
20g phosgene and 1g pyridines are passed through into 100g toluene at 0 DEG C, the above-mentioned reaction solution containing sodium salt is added dropwise, insulation is anti-
Answer 1 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
The above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is dense
Contracting, freezing and crystallizing, filtering, drying, obtain 29.0gN- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
After testing, the purity of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is 96.0%, yield
For 93.6%.
Embodiment 2
By 17.88 g4- trifluoro-methoxyanilines（99%, 0.10mol）It is dissolved in 100g toluene, is warming up to 50 DEG C of dropwise addition chloro-carbonic acids
Methyl esters 11.45g（99%, 0.12mol）, when insulation reaction 5 is small, washing, reflux water-dividing is obtained containing N- [(4- trifluoros to anhydrous
Methoxyl group) phenyl] methyl carbamate reaction solution.
Sampling detects, N- [(4- tri- in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Fluorine methoxyl group) phenyl] methyl carbamate mass content be 95.8%, moisture 0.08%.
The 9.8g tert-butyl alcohols are added into the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Sodium（98%, 0.10mol）, 110 DEG C of removing tert-butyl alcohols are warming up to, obtain the reaction solution containing sodium salt.
20g phosgene and 1g pyridines are passed through into 100g toluene at 0 DEG C, the above-mentioned reaction solution containing sodium salt is added dropwise, insulation is anti-
Answer 1 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
The above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is dense
Contracting, freezing and crystallizing, filtering, drying, obtain 28.5gN- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
After testing, the purity of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is 95%, and yield is
91%。
Embodiment 3
By 17.88g4- trifluoro-methoxyanilines（99%, 0.10mol）It is dissolved in 100g toluene, is warming up to 110 DEG C of dropwise addition chloro-carbonic acids
Methyl esters 11.45g（99%, 0.12mol）, when insulation reaction 1 is small, washing, reflux water-dividing is obtained containing N- [(4- trifluoros to anhydrous
Methoxyl group) phenyl] methyl carbamate reaction solution.
Sampling detects, N- [(4- tri- in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Fluorine methoxyl group) phenyl] methyl carbamate mass content be 96.6%, moisture 0.08%.
The 9.8g tert-butyl alcohols are added into the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Sodium（98%, 0.10mol）, 110 DEG C of removing tert-butyl alcohols are warming up to, obtain the reaction solution containing sodium salt.
20g phosgene and 1g pyridines are passed through into 100g toluene at 0 DEG C, the above-mentioned reaction solution containing sodium salt is added dropwise, insulation is anti-
Answer 1 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
The above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is dense
Contracting, freezing and crystallizing, filtering, drying, obtain 28.8gN- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
After testing, the purity of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is 95.5%, yield
For 92.4%.
Embodiment 4
By 17.88g4- trifluoro-methoxyanilines（99%, 0.10mol）It is dissolved in 100g toluene, is warming up to 80 DEG C of dropwise addition chloro-carbonic acids
Methyl esters 11.45g（99%, 0.12mol）, when insulation reaction 3 is small, washing, reflux water-dividing is obtained containing N- [(4- trifluoros to anhydrous
Methoxyl group) phenyl] methyl carbamate reaction solution.
Sampling detects, N- [(4- tri- in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Fluorine methoxyl group) phenyl] methyl carbamate mass content be 98.4%, moisture 0.08%.
The 11.4g tert-butyl alcohols are added into the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Potassium（98%, 0.10mol）, 110 DEG C of removing tert-butyl alcohols are warming up to, obtain the reaction solution containing sodium salt.
20g phosgene and 1g pyridines are passed through into 100g toluene at 0 DEG C, the above-mentioned reaction solution containing sodium salt is added dropwise, insulation is anti-
Answer 1 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
The above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is dense
Contracting, freezing and crystallizing, filtering, drying, obtain 29.1gN- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
After testing, the purity of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is 96.2%, yield
For 94%.
Comparative example 1
By 17.88g 4- trifluoro-methoxyanilines（99%, 0.10mol）, 100g toluene and 11g sodium acid carbonates（99%, 0.13mol）
Mixing, is warming up to 10 DEG C and methylchloroformate 11.45g is added dropwise（99%, 0.12mol）, when insulation reaction 3 is small, washing, reflux water-dividing
It is extremely anhydrous, obtain the reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate.
Sampling detects, N- [(4- tri- in the above-mentioned reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate
Fluorine methoxyl group) phenyl] methyl carbamate mass content be 96%, moisture 0.08%.
At 5 DEG C, sodium hydrogen 4g is added portionwise（60%, 0.10mol）, stirring 30 minutes is added, obtains the reaction containing sodium salt
Liquid.
It is small that 20g phosgene, 1g pyridines and the above-mentioned reaction solution containing sodium salt, insulation reaction 1 are passed through into 100g toluene at 0 DEG C
When, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
The above-mentioned reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is dense
Contracting, freezing and crystallizing, filtering, drying, obtain 29.3gN- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
After testing, the purity of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is 95.0%, yield
For 93.6%.
In process of production without using acid binding agent it can be seen from above-described embodiment and comparative example 1, but by reaction temperature
When bringing up to appropriate level, the purity of product can get a promotion, and labor substituting sodium hydrogen using sodium tert-butoxide or potassium tert-butoxide
After choline reagent, yield will not be influenced while production process is safer.
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
Apply all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, the scope that this specification is recorded all is considered to be.
Embodiment described above only expresses the several embodiments of the present invention, its description is more specific and detailed, but simultaneously
Cannot therefore it be construed as limiting the scope of the patent.It should be pointed out that come for those of ordinary skill in the art
Say, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the protection of the present invention
Scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (8)
- A kind of 1. synthetic method of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate, it is characterised in that Comprise the following steps：4- trifluoro-methoxyanilines are dissolved in toluene, are warming up to 50 DEG C ~ 110 DEG C, methylchloroformate, insulation reaction 1 ~ 5 is added dropwise Hour, washing, reflux water-dividing obtains the reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate to anhydrous；Activation base reagent, heating are added into the reaction solution containing N- [(4- trifluoromethoxies) phenyl] methyl carbamate To 100 DEG C ~ 110 DEG C removing tert-butyl alcohols, the reaction solution containing sodium salt is obtained；At 0 DEG C ~ 10 DEG C, phosgene is passed through into toluene, adds pyridine, the reaction solution containing sodium salt, insulation reaction 0.5 is added dropwise ~ 1.5 it is small when, obtain the reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate；The reaction solution containing N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate is washed, is concentrated, Freezing and crystallizing, filtering, drying, obtain the N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate.
- 2. the synthesis side of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 Method, it is characterised in that the activation base reagent is sodium tert-butoxide or potassium tert-butoxide.
- 3. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the molar ratio of the 4- trifluoro-methoxyanilines and the methylchloroformate is 1:1~1.5.
- 4. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the molar ratio of the 4- trifluoro-methoxyanilines and the activation base reagent is 1:1~1.5.
- 5. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the mass ratio of the phosgene and pyridine is：100：4~6.
- 6. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the condition of the concentration is：Temperature is 78 DEG C ~ 82 DEG C, and vacuum is -0.09MPa ~ 0.095MPa.
- 7. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the temperature of the freezing and crystallizing is -2 DEG C ~ 2 DEG C.
- 8. the conjunction of N- chloroformyls-N [(4- trifluoromethoxies) phenyl] methyl carbamate according to claim 1 or 2 Into method, it is characterised in that the condition of the drying is：Temperature is 55 DEG C ~ 65 DEG C, when the time is 22 ~ 26 small.
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| CN109369463A (en) * | 2018-12-05 | 2019-02-22 | 大连奇凯医药科技有限公司 | The preparation method of N- chloroformyl-N- [4- (trifluoromethoxy) phenyl] methyl carbamate |
| CN109535036A (en) * | 2018-12-26 | 2019-03-29 | 山东华阳农药化工集团有限公司 | A kind of synthetic method of indoxacarb intermediate chloroformyl [4- (trifluoromethoxy) phenyl] methyl carbamate |
| CN112479934A (en) * | 2020-12-09 | 2021-03-12 | 安徽广信农化股份有限公司 | Synthesis method of methyl amino chloroformate |
| CN113252831A (en) * | 2021-05-20 | 2021-08-13 | 京博农化科技有限公司 | Ultra-high performance liquid chromatography analysis method for N-chloroformyl-N- [4- (trifluoromethoxy) phenyl ] methyl carbamate |
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| CN109535036B (en) * | 2018-12-26 | 2021-05-25 | 山东华阳农药化工集团有限公司 | Synthetic method of indoxacarb intermediate methyl chloroformyl [4- (trifluoromethoxy) phenyl ] carbamate |
| CN112479934A (en) * | 2020-12-09 | 2021-03-12 | 安徽广信农化股份有限公司 | Synthesis method of methyl amino chloroformate |
| CN113252831A (en) * | 2021-05-20 | 2021-08-13 | 京博农化科技有限公司 | Ultra-high performance liquid chromatography analysis method for N-chloroformyl-N- [4- (trifluoromethoxy) phenyl ] methyl carbamate |
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