CN109627190B - Synthesis method of benzyl carbazate - Google Patents
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Abstract
The invention relates to the technical field of compound synthesis, in particular to a method for synthesizing benzyl carbazate, which comprises the following steps: dissolving hydrazine hydrate in a solvent, adding a catalyst, mixing and stirring for at least 5min, and introducing inert gas to discharge air; dropwise adding benzyl chloroformate into the reaction container in the first step, reacting at constant temperature of-20-30 ℃ for at least 2h, heating for reaction for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering, combining the filtrate and the washing solution, and distilling under reduced pressure to remove the solvent; and adding the residue after reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent to obtain the pure benzyl carbazate. The invention solves the problems of low yield of the prior benzyl carbazate and difficult purification of the product, and the prepared benzyl carbazate has the advantages of high yield, high purity and high material utilization rate.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a synthetic method of benzyl carbazate.
Background
Benzyl carbazate is an important organic intermediate, can be used for preparing plant protective agents and transaminase inhibitors, and has wide application in pesticide and medicine synthesis. The patent reports that dimethyl carbonate (DMC) and benzyl alcohol are subjected to complete vinegar exchange reaction to obtain binodal carbonate, and then the binodal carbonate is subjected to reaction with a hydrated cake to obtain the LINKY formic acid binodal vinegar, but the process yield is only 50%, the synthesis route is long, and the product purity is low.
Benzyl carbazate is known by the english name benzyl carbazate, the molecular formula is C8H10N2O2, the molecular weight is 166.18, CAS number: 5331-43-1, which is a serious injury to the eyes. The structural formula of benzyl carbazate is as follows:
chinese patent 201410055938.3 (a method for synthesizing benzyl carbazate) discloses a method for synthesizing benzyl carbazate, which mainly describes: a synthetic method of benzyl carbazate comprises the following steps: a) dissolving hydrazine hydrate in a solvent and adding alkali; b) controlling the reaction temperature to be-20-80 ℃, and dropwise adding benzyl chloroformate; c) carrying out salifying reaction on the obtained crude product, and removing impurities; and d) dissociating the obtained salt by using alkali to obtain the pure hydrazine benzyl formate. The method has the advantages of simple and convenient operation, good safety, high yield and low production cost, thereby meeting the large demand of the novel pesticide indoxacarb and other fine chemical products on the key intermediate hydrazine benzyl formate.
Chinese patent 200810031026.7 (a method for synthesizing benzyl carbazate) discloses a method for synthesizing benzyl carbazate, which mainly describes: the technological process of synthesizing benzyl carbazate in one step includes the reaction of dimethyl carbonate and hydrazine hydrate to form intermediate product methyl carbazate, and the reaction of adding benzyl alcohol in the presence of catalyst to obtain benzyl carbazate in one step. The invention has the advantages that the one-step method for synthesizing the hydrazino benzyl formate has the characteristics of simple process, high product yield and purity, low production cost and the like, and solves the problems that the raw material, the hydrazino methyl formate is not produced at home and the monopolized price in foreign markets is high.
In the prior art, the yield of the benzyl carbazate prepared by one-step synthesis is low, and the product is not easy to purify.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, provides a method for synthesizing benzyl carbazate, solves the problems that the yield of the benzyl carbazate is low and the product is not easy to purify in the prior art, and has the advantages of high yield, high purity and high material utilization rate of the prepared benzyl carbazate.
The purpose of the invention is realized by the following technical scheme:
a synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in a solvent, adding a catalyst, mixing and stirring for at least 5min, introducing inert gas to discharge air, and reacting under the protection of the inert gas in the subsequent reaction process;
step two, dropwise adding benzyl chloroformate into the reaction container in the step one, reacting at constant temperature of-20-30 ℃ for at least 2h, heating to 80-120 ℃ for reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing filter residue for 2-3 times by using a solvent, combining the filtrate and a washing solution, and distilling under reduced pressure to remove the solvent;
and step three, adding the residue after reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min, placing the mixture in a salt bath for standing for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent to obtain the pure benzyl carbazate.
In the synthetic method of the benzyl carbazate, the reaction temperature is controlled to be-20-30 ℃ after the early-stage dropwise addition is finished, side reactions are less under the condition of lower temperature, the product purity is improved, and the product yield is improved; the purification process comprises the steps of firstly carrying out ultrasonic washing by using purified water, removing impurities dissolved in the water, standing by using an ice salt bath after ultrasonic washing to separate out a solid substance with higher purity, and then purifying the solid substance again by using methanol to obtain the product with high purity.
The chemical reaction formula of the synthesis method is as follows:
further, the hydrazine hydrate, the catalyst and benzyl chloroformate are sequentially (2.0-6.0) in molar weight ratio: (0.20-0.30): (1.0-1.2).
Further, the hydrazine hydrate, the catalyst and benzyl chloroformate are sequentially mixed according to a molar weight ratio of 4.0: 0.25: 1.0.
further, the hydrazine hydrate and the solvent are sequentially 1: (6-8).
Further, the solvent in the first step is one of toluene, tetrahydrofuran, dichloromethane, n-hexane, petroleum ether, ethyl acetate or acetonitrile;
and the solvent adopted for washing in the second step is one of toluene, tetrahydrofuran, dichloromethane, normal hexane, petroleum ether, ethyl acetate or acetonitrile.
In the synthetic method of the benzyl carbazinate, the solvent is selected from one of toluene, tetrahydrofuran, dichloromethane, normal hexane, petroleum ether, ethyl acetate or acetonitrile, the dissolving effect is good, the solvent is easy to recycle, the utilization rate of the solvent is improved, and the production cost is reduced; the same solvent is used in the first step and the second step, so that the low purity of the solvent recovered by later distillation is avoided.
Further, in the first step, the catalyst is one of potassium carbonate, sodium carbonate, lithium carbonate, triethylamine, potassium hydroxide or sodium hydroxide; and in the first step, the inert gas is helium or nitrogen.
In the method for synthesizing the benzyl carbazate, hydrazine is dissolved in an organic solvent, a catalyst is added after uniform mixing, and inert gas is introduced to exhaust air, so that the increase of side reactions caused by the existence of oxygen is avoided, and the yield of the product is reduced.
Further, the dropping temperature of the benzyl chloroformate in the second step is 20-30 ℃, and the dropping time is 10-15 min; and in the second step, the temperature of reduced pressure distillation is 40-50 ℃, and the pressure of reduced pressure distillation is 0.05-0.08 MPa.
Further, the temperature of the ice salt bath in the third step is-15-0 ℃; in the third step, the ultrasonic temperature is 30-45 ℃, and the ultrasonic frequency is 25-35 kHz; and the volatilization temperature of the methanol in the third step is 65-67 ℃.
The invention has the beneficial effects that:
1. in the method for synthesizing the benzyl carbazate, hydrazine is dissolved in an organic solvent, a catalyst is added after uniform mixing, and inert gas is introduced to exhaust air, so that the increase of side reactions caused by the existence of oxygen is avoided, and the yield of the product is reduced;
2. in the synthetic method of the benzyl carbazinate, the solvent is selected from one of toluene, tetrahydrofuran, dichloromethane, normal hexane, petroleum ether, ethyl acetate or acetonitrile, the dissolving effect is good, the solvent is easy to recycle, the utilization rate of the solvent is improved, and the production cost is reduced; the same solvent is used in the first step and the second step, so that the low purity of the solvent recovered by later-stage distillation is avoided;
3. in the synthetic method of the benzyl carbazate, the reaction temperature is controlled to be-20-30 ℃ after the early-stage dropwise addition is finished, side reactions are less under the condition of lower temperature, the product purity is improved, and the product yield is improved; the purification process comprises the steps of firstly carrying out ultrasonic washing by using purified water, removing impurities dissolved in the water, standing by using an ice salt bath after ultrasonic washing to separate out a solid substance with higher purity, and then purifying the solid substance again by using methanol to obtain the product with high purity.
Drawings
FIG. 1 is an infrared spectrum of benzyl carbazate;
FIG. 2 is a mass spectrum of benzyl carbazate.
Detailed Description
The technical solution of the present invention is further described in detail with reference to the following specific examples, but the scope of the present invention is not limited to the following.
Example 1
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in toluene, adding potassium carbonate, mixing and stirring for at least 5min, introducing helium gas to discharge air, and reacting in the subsequent reaction process under the protection of inert gas, wherein the weight ratio of hydrazine hydrate to solvent is 1: 6;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 20 ℃, the dripping time is 15min, after the dripping is finished, reacting at a constant temperature of-20 ℃ for at least 2h, heating to 80 ℃, reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 2 times by using toluene, combining the filtrate and the washing solution, distilling under reduced pressure to remove the solvent, wherein the temperature of the distillation under reduced pressure is 40 ℃, the pressure of the distillation under reduced pressure is 0.05MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 2.0 according to the molar weight ratio: 0.20: 1.0;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 30 ℃ and the ultrasonic frequency of 25kHz, standing in a ice salt bath for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent, wherein the exertion temperature of the methanol is 65-67 ℃, so as to obtain the pure benzyl carbazate.
Example 2
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in tetrahydrofuran, adding potassium hydroxide, mixing and stirring for at least 5min, introducing nitrogen to discharge air, and reacting in the subsequent reaction process under the protection of inert gas, wherein the hydrazine hydrate and the solvent are sequentially 1: 7;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 25 ℃, the dripping time is 12min, after the dripping is finished, reacting at a constant temperature of 0 ℃ for at least 2h, heating to 90 ℃, reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 3 times by using tetrahydrofuran, combining the filtrate and the washing solution, and then distilling under reduced pressure to remove the solvent, wherein the temperature of the distillation under reduced pressure is 45 ℃, the pressure of the distillation under reduced pressure is 0.07MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 3.0 according to the molar weight ratio: 0.25: 1.1;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 35 ℃ and the ultrasonic frequency of 30kHz, standing in a ice salt bath for at least 30min, wherein the temperature of the ice salt bath is-15-0 ℃, separating and removing supernatant, adding methanol for dissolution, volatilizing the methanol to the full extent, and performing the methanol at the exertion temperature of 65-67 ℃ to obtain the pure benzyl carbazate.
Example 3
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in dichloromethane, adding sodium carbonate, mixing and stirring for at least 5min, introducing helium gas to discharge air, and reacting in the subsequent reaction process under the protection of inert gas, wherein the hydrazine hydrate and a solvent are sequentially 1: 8;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 30 ℃, the dripping time is 10min, after the dripping is finished, reacting at a constant temperature of 10 ℃ for at least 2h, heating to 110 ℃, reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 3 times by using dichloromethane, combining the filtrate and the washing solution, and then distilling under reduced pressure to remove the solvent, wherein the temperature of the distillation under reduced pressure is 50 ℃, the pressure of the distillation under reduced pressure is 0.05MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 6.0 according to the molar weight ratio: 0.30: 1.2;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 40 ℃ and the ultrasonic frequency of 35kHz, standing in a ice salt bath for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent, wherein the exertion temperature of the methanol is 65-67 ℃, so as to obtain the pure benzyl carbazate.
Example 4
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in ethyl acetate, adding a catalyst, mixing and stirring for at least 5min, introducing lithium carbonate to discharge air, and reacting in the subsequent reaction process under the protection of nitrogen, wherein the hydrazine hydrate and the solvent are sequentially 1: 8;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 30 ℃, the dripping time is 15min, after the dripping is finished, reacting at a constant temperature of 30 ℃ for at least 2h, heating to 120 ℃ for reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 3 times by using ethyl acetate, combining the filtrate and the washing solution, and then distilling under reduced pressure to remove the solvent, wherein the temperature of the distillation under reduced pressure is 50 ℃, the pressure of the distillation under reduced pressure is 0.05MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 4.0 according to the molar weight ratio: 0.25: 1.0;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 45 ℃ and the ultrasonic frequency of 35kHz, standing in a ice salt bath for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent, wherein the exertion temperature of the methanol is 65-67 ℃, so as to obtain the pure benzyl carbazate.
Example 5
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in acetonitrile, adding sodium hydroxide, mixing and stirring for at least 5min, introducing helium gas to discharge air, and reacting in the subsequent reaction process under the protection of inert gas, wherein the hydrazine hydrate and the solvent are sequentially 1: 8;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 30 ℃, the dripping time is 10min, after the dripping is finished, reacting at a constant temperature of 30 ℃ for at least 2h, heating to 120 ℃ for reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 3 times by using acetonitrile, combining the filtrate and the washing solution, and then distilling under reduced pressure to remove the solvent, wherein the temperature of the distillation under reduced pressure is 50 ℃, the pressure of the distillation under reduced pressure is 0.05MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 3.0 according to the molar weight ratio: 0.28: 1.1;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 45 ℃ and the ultrasonic frequency of 30kHz, standing in a ice salt bath for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent, wherein the exertion temperature of the methanol is 65-67 ℃, so as to obtain the pure benzyl carbazate.
Example 6
A synthetic method of benzyl carbazate comprises the following steps:
step one, dissolving hydrazine hydrate in n-hexane, adding triethylamine, mixing and stirring for at least 5min, introducing inert gas to discharge air, and reacting in the subsequent reaction process under the protection of nitrogen, wherein the hydrazine hydrate and a solvent are sequentially 1: 8;
step two, dripping benzyl chloroformate into the reaction container in the step one, wherein the dripping temperature is 25 ℃, the dripping time is 12min, after the dripping is finished, reacting at a constant temperature of-10 ℃ for at least 2h, heating to 120 ℃, reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing the filter residue for 3 times by using normal hexane, combining the filtrate and the washing solution, distilling under reduced pressure to remove the solvent, wherein the temperature of the reduced pressure distillation is 50 ℃, the pressure of the reduced pressure distillation is 0.05MPa, and the hydrazine hydrate, the catalyst and the benzyl chloroformate are sequentially 5.0 according to the molar weight ratio: 0.28: 1.1;
and step three, adding the residue obtained after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min at the ultrasonic temperature of 45 ℃ and the ultrasonic frequency of 30kHz, standing in a ice salt bath for at least 30min, separating and removing supernatant, adding methanol for dissolving, and volatilizing the methanol to the full extent, wherein the exertion temperature of the methanol is 65-67 ℃, so as to obtain the pure benzyl carbazate.
Example 1-example 6 the purity and yield of benzyl carbazate and solvent recovery are shown in table 1:
| examples | 1 | 2 | 3 | 4 | 5 | 6 |
| Purity/% of benzyl carbazate | 99.5 | 99.6 | 99.6 | 99.6 | 99.5 | 99.4 |
| Yield of benzyl carbazate/% | 92 | 93 | 95 | 95 | 94 | 93 |
| Solvent recovery/% | 90 | 90 | 90 | 92 | 91 | 89 |
TABLE 1
The foregoing is illustrative of the preferred embodiments of this invention, and it is to be understood that the invention is not limited to the precise form disclosed herein and that various other combinations, modifications, and environments may be resorted to, falling within the scope of the concept as disclosed herein, either as described above or as apparent to those skilled in the relevant art. And that modifications and variations may be effected by those skilled in the art without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (4)
1. A synthetic method of benzyl carbazate is characterized by comprising the following steps:
step one, dissolving hydrazine hydrate in a solvent, adding a catalyst, mixing and stirring for at least 5min, introducing inert gas to discharge air, and reacting under the protection of the inert gas in the subsequent reaction process;
step two, dropwise adding benzyl chloroformate into the reaction container in the step one, reacting at constant temperature of-20-30 ℃ for at least 2h, heating to 80-120 ℃ for reacting for at least 30min, cooling to below 80 ℃, standing for at least 30min, filtering at normal pressure to obtain filtrate, washing filter residue for 2-3 times by using a solvent, combining the filtrate and a washing solution, and distilling under reduced pressure to remove the solvent;
thirdly, adding the residue after the reduced pressure distillation into purified water, performing ultrasonic treatment for at least 5min, placing the mixture in a salt bath for standing for at least 30min, separating and removing supernatant, adding methanol for dissolution, and volatilizing the methanol to the full extent to obtain a pure product of benzyl carbazinate;
in the first step, the solvent is one of toluene, tetrahydrofuran, dichloromethane, n-hexane, petroleum ether, ethyl acetate or acetonitrile;
the solvent adopted for washing in the second step is one of toluene, tetrahydrofuran, dichloromethane, normal hexane, petroleum ether, ethyl acetate or acetonitrile;
the hydrazine hydrate, the catalyst and benzyl chloroformate are sequentially (2.0-6.0) in molar weight ratio: (0.20-0.30): (1.0-1.2);
the hydrazine hydrate and the solvent are sequentially 1: (6-8);
in the first step, the catalyst is one of potassium carbonate, sodium carbonate, lithium carbonate, triethylamine, potassium hydroxide or sodium hydroxide; and in the first step, the inert gas is helium or nitrogen.
2. The method for synthesizing benzyl carbazate according to claim 1, wherein the hydrazine hydrate, the catalyst and benzyl chloroformate are sequentially in a molar weight ratio of 4.0: 0.25: 1.0.
3. the method for synthesizing benzyl carbazate according to claim 1, wherein the dropping temperature of benzyl chloroformate in the second step is 20-30 ℃ and the dropping time is 10-15 min; and in the second step, the temperature of reduced pressure distillation is 40-50 ℃, and the pressure of reduced pressure distillation is 0.05-0.08 MPa.
4. The synthesis method of benzyl carbazate according to claim 1, wherein the temperature of the salt bath in step three is-15 to 0 ℃; in the third step, the ultrasonic temperature is 30-45 ℃, and the ultrasonic frequency is 25-35 kHz; and the volatilization temperature of the methanol in the third step is 65-67 ℃.
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