CN109627190A - A kind of synthetic method of hydrazino benzyl formate - Google Patents
A kind of synthetic method of hydrazino benzyl formate Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
Abstract
The present invention relates to compound synthesis technical fields, and in particular to a kind of synthetic method of hydrazino benzyl formate includes the following steps: for hydrazine hydrate to be dissolved in solvent, adds after catalyst after at least 5min is mixed, is passed through inert gas and carries out discharge air；Benzyl chloroformate is added dropwise in the reaction vessel in step 1, at being -20 ~ 30 DEG C in temperature after isothermal reaction at least 2h, temperature reaction at least 30min stands at least 30min after being cooled to 80 DEG C or less, filtering, vacuum distillation removes solvent after filtrate and cleaning solution are merged；Ultrasound at least 5min in purified water is added in residue after vacuum distillation, is separated off supernatant, after adding methanol dissolution, volatilization methanol is to the greatest extent to get sterling hydrazino benzyl formate.The present invention solves the problems, such as that the yield of existing middle hydrazino benzyl formate is lower and product not easy purification, the high advantage of hydrazino benzyl formate high income, purity is high and the material utilization being prepared.
Description
Technical field
The present invention relates to compound synthesis technical fields, and in particular to a kind of synthetic method of hydrazino benzyl formate.
Background technique
Hydrazino benzyl formate is a kind of important organic intermediate, can be used for preparing plant protection product and transaminase inhibits
Agent has in pesticide and medicine synthesis and has been widely used.There is patent report to be carried out with carbonic acid diformazan vinegar (DMC) with benzyl alcohol
Full vinegar exchange reaction, obtains two section vinegar of carbonic acid, then reacts to obtain unicorn base formic acid section Cu Shi, but the process recovery ratio with hydration cake again
Only 50%, and synthetic route is long, product purity is low.
The English name of hydrazino benzyl formate is benzyl carbazate, and molecular formula is C8H10N2O2, and molecular weight is
166.18, No. CAS: 5331-43-1, which has grievous injury to eyes.The structural formula of hydrazino benzyl formate is as follows:
Hydrazino benzyl formate is disclosed in Chinese patent 201410055938.3 (synthetic method of hydrazino benzyl formate)
A kind of synthetic method, mainly describes: a kind of synthetic method of hydrazino benzyl formate comprising following steps: a), by hydrazine hydrate
It is dissolved in solvent and alkali is added；B), under conditions of control reaction temperature is -20 DEG C~80 DEG C, benzyl chloroformate is added dropwise；C), will
After obtained crude product carries out salt-forming reaction, impurity is removed；And d), by obtained salt alkaline hydrolysis from rear, obtain sterling diazanyl first
Acid benzyl ester.Its is easy to operate, safety is good, yield is high, production cost is low, to meet new pesticide indoxacarb and other are fine
Chemical products volume production is to key intermediate-hydrazino benzyl formate wilderness demand.
Hydrazino benzyl formate is disclosed in Chinese patent 200810031026.7 (synthetic method of hydrazino benzyl formate)
A kind of synthetic method, mainly describes: the process of one-step synthesis method hydrazino benzyl formate, by dimethyl carbonate and hydrazine hydrate
Reaction forms intermediate product methyl hydrazinocarboxylate and does not isolate and purify, and directly plus benzyl alcohol reacts a step under the action of catalyst and obtains
To hydrazino benzyl formate.It is an advantage of the invention that there is technique letter using the process of one-step synthesis method hydrazino benzyl formate
The features such as single, product yield high-purity height, production cost is low, solves the raw material methyl hydrazinocarboxylate country without production, external city
The problem of field monopoly price valuableness.
In the prior art, the yield for preparing hydrazino benzyl formate by one-step synthesis method is lower, product not easy purification.
Summary of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of synthetic method of hydrazino benzyl formate, solutions
Determined existing middle hydrazino benzyl formate yield is lower and product not easy purification the problem of, the hydrazino benzyl formate being prepared is received
The advantage that rate is high, purity is high and material utilization are high.
The purpose of the present invention is achieved through the following technical solutions:
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in solvent, adds after catalyst after at least 5min is mixed, be passed through indifferent gas
Body carries out discharge air, is reacted under the protection of inert gas in reaction process later；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, constant temperature at being -20~30 DEG C in temperature
After reacting at least 2h, 80~120 DEG C of reaction at least 30min are warming up to, stand at least 30min, normal pressure after being cooled to 80 DEG C or less
Filtrate is obtained by filtration, is washed filter residue 2~3 times using solvent, vacuum distillation removes solvent after filtrate and cleaning solution are merged；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, it is placed in ice salt bath and stands
After at least 30min, it is separated off supernatant, after adding methanol dissolution, volatilization methanol is to the greatest extent to get sterling carbazic acid benzyl
Ester.
The synthetic method mid-early stage of hydrazino benzyl formate is added dropwise to complete rear reaction temperature control at -20~30 DEG C, lower
Side reaction is less in the case where temperature, improves product purity and improves the yield of product；Purification process first uses purified water ultrasonic
Washing, impurity soluble in water is removed, and is stood after ultrasound using ice salt bath and solids is precipitated, and purity is higher, then by solid
Object is purified again using methanol, and the product purity finally obtained is high.
The chemical equation of above-mentioned synthetic method are as follows:
Further, the hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by (2.0~6.0) according to mole ratio:
(0.20~0.30): (1.0~1.2).
Further, the hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by 4.0:0.25 according to mole ratio:
1.0。
Further, the hydrazine hydrate and solvent are followed successively by 1:(6~8 according to weight ratio).
Further, solvent is toluene, tetrahydrofuran, methylene chloride, n-hexane, petroleum ether, acetic acid in the step 1
One of ethyl ester or acetonitrile；
The solvent used is washed in the step 2 as toluene, tetrahydrofuran, methylene chloride, n-hexane, petroleum ether, acetic acid
One of ethyl ester or acetonitrile.
Solvent selection toluene in the synthetic method of hydrazino benzyl formate, tetrahydrofuran, methylene chloride, n-hexane, petroleum ether,
One of ethyl acetate or acetonitrile, solute effect is good, and is easily recycled, and improves the utilization rate of solvent, reduces
Production cost；Identical solvent is used in step 1 and step 2, the solvent purity for avoiding the later period from being distilled to recover is low.
Further, catalyst is potassium carbonate, sodium carbonate, lithium carbonate, triethylamine, potassium hydroxide or hydrogen in the step 1
One of sodium oxide molybdena；Inert gas is helium or nitrogen in the step 1.
First hydrazine is dissolved in organic solvent in the synthetic method of hydrazino benzyl formate, catalyst is added after being uniformly mixed,
It is passed through inert gas discharge air, oxygen is avoided in the presence of causing side reaction to increase, reduces the yield of product, the indifferent gas of use
Body is helium or nitrogen, helium or nitrogen be difficult to benzyl chloroformate or hydrazine reaction, reduce the generation of side reaction, reduce production
Impurity in object improves product purity and improves the yield of product.
Further, in the step 2 benzyl chloroformate dropping temperature be 20~30 DEG C, time for adding be 10~
15min；The temperature being evaporated under reduced pressure in the step 2 is 40~50 DEG C, and the pressure of vacuum distillation is 0.05~0.08MPa.
Further, the temperature of ice salt bath is -15~0 DEG C in the step 3；Ultrasonic temperature is 30 in the step 3
~45 DEG C, supersonic frequency is 25~35kHz；The volatilization temperature of methanol is 65~67 DEG C in the step 3.
The beneficial effects of the present invention are:
1. first hydrazine is dissolved in organic solvent in the synthetic method of hydrazino benzyl formate, catalysis is added after being uniformly mixed
Agent is passed through inert gas discharge air, and avoiding oxygen and existing causes side reaction to increase, and reduces the yield of product, use it is lazy
Property gas be helium or nitrogen, helium or nitrogen be difficult to benzyl chloroformate or hydrazine reaction, reduce the generation of side reaction, reduce
Impurity in product, improves product purity and improves the yield of product；
2. solvent selection toluene, tetrahydrofuran, methylene chloride, n-hexane, petroleum in the synthetic method of hydrazino benzyl formate
One of ether, ethyl acetate or acetonitrile, solute effect is good, and is easily recycled, and improves the utilization rate of solvent, drop
Low production cost；Identical solvent is used in step 1 and step 2, the solvent purity for avoiding the later period from being distilled to recover is low；
3. the synthetic method mid-early stage of hydrazino benzyl formate is added dropwise to complete the control of rear reaction temperature at -20~30 DEG C, compared with
Side reaction is less in the case where low temperature, improves product purity and improves the yield of product；Purification process is first super with purified water
Sound washing, impurity soluble in water is removed, and is stood after ultrasound using ice salt bath and solids is precipitated, purity is higher, then will consolidate
Body object is purified again using methanol, and the product purity finally obtained is high.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of hydrazino benzyl formate；
Fig. 2 is the mass spectrogram of hydrazino benzyl formate.
Specific embodiment
Technical solution of the present invention is described in further detail combined with specific embodiments below, but protection scope of the present invention is not
It is confined to as described below.
Embodiment 1
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in toluene, add after potassium carbonate after at least 5min is mixed, be passed through helium into
Row discharge air, is reacted under the protection of inert gas in reaction process later, and wherein hydrazine hydrate and solvent are according to weight
Amount ratio is followed successively by 1:6；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 20 DEG C, time for adding
80 DEG C of reaction at least 30min are warming up to, are dropped at being -20 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 15min
Temperature to standing at least 30min, natural filtration after 80 DEG C or less obtains filtrate, is washed filter residue 2 times using toluene, by filtrate and washing
Vacuum distillation removes solvent after liquid merges, and the temperature of vacuum distillation is 40 DEG C, and the pressure of vacuum distillation is 0.05MPa, wherein water
It closes hydrazine, catalyst and benzyl chloroformate and is followed successively by 2.0:0.20:1.0 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, ultrasonic temperature is 30 DEG C, is surpassed
Acoustic frequency is 25kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Embodiment 2
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in tetrahydrofuran, adds after potassium hydroxide after at least 5min is mixed, be passed through
Nitrogen carries out discharge air, is reacted under the protection of inert gas in reaction process later, wherein hydrazine hydrate and solvent
1:7 is followed successively by according to weight ratio；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 25 DEG C, time for adding
90 DEG C of reaction at least 30min are warming up to, are cooled down at being 0 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 12min
At least 30min is stood after to 80 DEG C or less, natural filtration obtains filtrate, washs filter residue 3 times using tetrahydrofuran, by filtrate and washes
It washs vacuum distillation after liquid merges and removes solvent, the temperature of vacuum distillation is 45 DEG C, and the pressure of vacuum distillation is 0.07MPa, wherein
Hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by 3.0:0.25:1.1 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, it is 35 DEG C of ultrasonic temperature, ultrasonic
Frequency is 30kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Embodiment 3
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in methylene chloride, adds after sodium carbonate after at least 5min is mixed, be passed through helium
Gas carries out discharge air, is reacted under the protection of inert gas in reaction process later, wherein hydrazine hydrate and solvent are pressed
1:8 is followed successively by according to weight ratio；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 30 DEG C, time for adding
110 DEG C of reaction at least 30min are warming up to, are dropped at being 10 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 10min
Temperature obtains filtrate at least 30min, natural filtration is stood after 80 DEG C or less, is washed filter residue 3 times using methylene chloride, by filtrate and
Vacuum distillation removes solvent after cleaning solution merges, and the temperature of vacuum distillation is 50 DEG C, and the pressure of vacuum distillation is 0.05MPa,
Middle hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by 6.0:0.30:1.2 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, ultrasonic temperature is 40 DEG C, is surpassed
Acoustic frequency is 35kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Embodiment 4
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in ethyl acetate, adds after catalyst after at least 5min is mixed, be passed through carbon
Sour lithium carries out discharge air, is reacted under the protection of nitrogen in reaction process later, wherein hydrazine hydrate and solvent according to
Weight ratio is followed successively by 1:8；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 30 DEG C, time for adding
120 DEG C of reaction at least 30min are warming up to, are dropped at being 30 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 15min
Temperature obtains filtrate at least 30min, natural filtration is stood after 80 DEG C or less, is washed filter residue 3 times using ethyl acetate, by filtrate and
Vacuum distillation removes solvent after cleaning solution merges, and the temperature of vacuum distillation is 50 DEG C, and the pressure of vacuum distillation is 0.05MPa,
Middle hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by 4.0:0.25:1.0 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, ultrasonic temperature is 45 DEG C, is surpassed
Acoustic frequency is 35kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Embodiment 5
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in acetonitrile, adds after sodium hydroxide after at least 5min is mixed, be passed through helium
Carry out discharge air, reacted under the protection of inert gas in reaction process later, wherein hydrazine hydrate and solvent according to
Weight ratio is followed successively by 1:8；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 30 DEG C, time for adding
120 DEG C of reaction at least 30min are warming up to, are dropped at being 30 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 10min
Temperature to standing at least 30min, natural filtration after 80 DEG C or less obtains filtrate, is washed filter residue 3 times using acetonitrile, by filtrate and washing
Vacuum distillation removes solvent after liquid merges, and the temperature of vacuum distillation is 50 DEG C, and the pressure of vacuum distillation is 0.05MPa, wherein water
It closes hydrazine, catalyst and benzyl chloroformate and is followed successively by 3.0:0.28:1.1 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, ultrasonic temperature is 45 DEG C, is surpassed
Acoustic frequency is 30kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Embodiment 6
A kind of synthetic method of hydrazino benzyl formate, includes the following steps:
Step 1: hydrazine hydrate is dissolved in n-hexane, adds after triethylamine after at least 5min is mixed, be passed through inertia
Gas carries out discharge air, is reacted under the protection of nitrogen in reaction process later, wherein hydrazine hydrate and solvent according to
Weight ratio is followed successively by 1:8；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, dropping temperature is 25 DEG C, time for adding
120 DEG C of reaction at least 30min are warming up to, are dropped at being -10 DEG C in temperature after being added dropwise to complete after isothermal reaction at least 2h for 12min
Temperature to standing at least 30min, natural filtration after 80 DEG C or less obtains filtrate, is washed filter residue 3 times using n-hexane, by filtrate and is washed
It washs vacuum distillation after liquid merges and removes solvent, the temperature of vacuum distillation is 50 DEG C, and the pressure of vacuum distillation is 0.05MPa, wherein
Hydrazine hydrate, catalyst and benzyl chloroformate are followed successively by 5.0:0.28:1.1 according to mole ratio；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, ultrasonic temperature is 45 DEG C, is surpassed
Acoustic frequency is 30kHz, is placed in ice salt bath after standing at least 30min, and the temperature of ice salt bath is -15~0 DEG C, is separated off supernatant
Liquid, after adding methanol dissolution, for volatilization methanol to the greatest extent, the performance temperature of methanol is 65~67 DEG C to get sterling carbazic acid benzyl
Ester.
Purity and yield and the solvent recovering rate such as table 1 for the hydrazino benzyl formate that embodiment 1- embodiment 6 is prepared
It is shown:
| Embodiment | 1 | 2 | 3 | 4 | 5 | 6 |
| Hydrazino benzyl formate purity/% | 99.5 | 99.6 | 99.6 | 99.6 | 99.5 | 99.4 |
| Hydrazino benzyl formate yield/% | 92 | 93 | 95 | 95 | 94 | 93 |
| Solvent recovering rate/% | 90 | 90 | 90 | 92 | 91 | 89 |
Table 1
The above is only a preferred embodiment of the present invention, it should be understood that the present invention is not limited to described herein
Form should not be regarded as an exclusion of other examples, and can be used for other combinations, modifications, and environments, and can be at this
In the text contemplated scope, modifications can be made through the above teachings or related fields of technology or knowledge.And those skilled in the art institute into
Capable modifications and changes do not depart from the spirit and scope of the present invention, then all should be in the protection scope of appended claims of the present invention
It is interior.
Claims (8)
1. a kind of synthetic method of hydrazino benzyl formate, which comprises the steps of:
Step 1: hydrazine hydrate is dissolved in solvent, add after catalyst after at least 5min is mixed, be passed through inert gas into
Row discharge air, is reacted under the protection of inert gas in reaction process later；
Step 2: benzyl chloroformate is added dropwise in the reaction vessel in step 1, isothermal reaction at being -20 ~ 30 DEG C in temperature
After at least 2h, 80 ~ 120 DEG C of reaction at least 30min are warming up to, stand at least 30min after being cooled to 80 DEG C or less, natural filtration obtains
It to filtrate, is washed filter residue 2 ~ 3 times using solvent, vacuum distillation removes solvent after filtrate and cleaning solution are merged；
Step 3: ultrasound at least 5min in purified water is added in the residue after vacuum distillation, it is placed in ice salt bath and stands at least
After 30min, it is separated off supernatant, after adding methanol dissolution, volatilization methanol is to the greatest extent to get sterling hydrazino benzyl formate.
2. a kind of synthetic method of hydrazino benzyl formate according to claim 1, which is characterized in that the hydrazine hydrate is urged
Agent and benzyl chloroformate are followed successively by (2.0 ~ 6.0) according to mole ratio: (0.20 ~ 0.30): (1.0 ~ 1.2).
3. a kind of synthetic method of hydrazino benzyl formate according to claim 1 or 2, which is characterized in that the hydrazine hydrate,
Catalyst and benzyl chloroformate are followed successively by 4.0:0.25:1.0 according to mole ratio.
4. a kind of synthetic method of hydrazino benzyl formate according to claim 1, which is characterized in that the hydrazine hydrate and molten
Agent is followed successively by 1:(6 ~ 8 according to weight ratio).
5. a kind of synthetic method of hydrazino benzyl formate according to claim 1, it is characterised in that:
Solvent is in toluene, tetrahydrofuran, methylene chloride, n-hexane, petroleum ether, ethyl acetate or acetonitrile in the step 1
It is a kind of；
The solvent used is washed in the step 2 as toluene, tetrahydrofuran, methylene chloride, n-hexane, petroleum ether, ethyl acetate
Or one of acetonitrile.
6. a kind of synthetic method of hydrazino benzyl formate according to claim 1 or 4, which is characterized in that the step 1
Middle catalyst is one of potassium carbonate, sodium carbonate, lithium carbonate, triethylamine, potassium hydroxide or sodium hydroxide；In the step 1
Inert gas is helium or nitrogen.
7. a kind of synthetic method of hydrazino benzyl formate according to claim 1 or 5, which is characterized in that the step 2
The dropping temperature of middle benzyl chloroformate is 20 ~ 30 DEG C, and time for adding is 10 ~ 15min；The temperature being evaporated under reduced pressure in the step 2
It is 40 ~ 50 DEG C, the pressure of vacuum distillation is 0.05 ~ 0.08MPa.
8. a kind of synthetic method of hydrazino benzyl formate according to claim 1, which is characterized in that ice in the step 3
The temperature of salt bath is -15 ~ 0 DEG C；Ultrasonic temperature is 30 ~ 45 DEG C in the step 3, and supersonic frequency is 25 ~ 35kHz；The step
The volatilization temperature of methanol is 65 ~ 67 DEG C in three.
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| CN109627190B (en) | 2021-03-09 |
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