CN106278927A - A kind of 2 amino 4 bromine N, the synthetic method of 5 dimethyl benzamides - Google Patents
A kind of 2 amino 4 bromine N, the synthetic method of 5 dimethyl benzamides Download PDFInfo
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
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Abstract
The invention discloses a kind of 2 amino 4 bromine N, the synthetic method of 5 dimethyl benzamides, belong to the field of chemical synthesis.The present invention is first with 2 nitro 5 ar-Toluic acids as raw material, utilize ferric chloride (FeCl36H2O) and palladium for composite catalyst, add hydrazine hydrate solution and carry out reduction reaction, obtain 2 amino 5 ar-Toluic acids, by itself and dichloromethane, under pyridine is catalyst, add two (trichloromethyl) carbonic ester tetrahydrofuran solution and carry out cyclization, reaction terminates rear microwave heating to backflow, add methylamine water solution after backflow and carry out methylamine reaction, obtain 2 amino N, 5 dimethyl benzamides, it is carried out halogenating reaction under conditions of last and hydrogen peroxide and hydrobromic acid solution and obtains 2 amino 4 bromine N, 5 dimethyl benzamides.
Description
Technical field
The invention discloses a kind of 2-bromo-N of amino-4-, the synthetic method of 5-dimethyl benzamide, belong to chemosynthesis
Field.
Background technology
The class developed in recent years is adjacent formamido group benzene to the preventing and treating preferable novel pesticide of lepidoptera pest effect
Methanamide, this insecticides is widely studied because of its low toxicity, low-residual, mechanism of action uniqueness.It is reported, this insecticides is prevented
The cardinal principle controlling insect is the ryanodine receptor of activation insecticide.Ryanodine receptor is referred to as calciphorin, activation insecticide
Even if ryanodine receptor insect cell calcium channel is in open state, causes the loss of a large amount of calcium ion, and then make insecticide
Muscle contraction until death.
Summary of the invention
The present invention provides the 2-bromo-N of amino-4-that a kind of reaction condition is gentle, yield is high, the conjunction of 5-dimethyl benzamide
One-tenth method.
For reaching above-mentioned purpose, the 2-bromo-N of amino-4-of the present invention, the synthetic route of 5-dimethyl benzamide is:
The 2-bromo-N of amino-4-that the present invention relates to, the building-up process of 5-dimethyl benzamide comprises the following steps:
(1) in the four-hole boiling flask of 500mL, it is sequentially added into 120～150mL deionized waters, 20～22g2-nitro-5-methylbenzene first
Acid, 10～12g sodium hydroxide, 20～22g ferric chloride (FeCl36H2O) and 0.1～0.2g palladium, put into water-bath by four-hole boiling flask after addition
In Guo, rise high-temperature and drip 13～15mL mass fraction 60% hydrazine hydrate aqueous solutions to 75～80 DEG C of backward flasks, control dropping
Speed is 3～5mL/min, insulated and stirred reaction 5～7h after completion of dropwise addition, and reactant is filtered after cooling down room temperature after terminating by reaction
Obtaining filtrate, and be 7.0 with mass fraction 20% hydrochloric acid regulation filtrate pH, the stirring 60～80min after regulation, after stirring, sucking filtration obtains
Filtering residue, and put in baking oven after deionized water rinsing 3～5 times, is dried 6～10h at 60～70 DEG C, and dried 2-amino-
5-ar-Toluic acid；
(2) equipped with agitator, condensing tube, thermometer, constant pressure funnel 500mL four-hole boiling flask in add above-mentioned 2-ammonia
Base-5-ar-Toluic acid solid and 200～250mL dichloromethane, 0.3～0.5mL pyridine, put into oil by four-hole boiling flask after addition
In bath, in flask, when being increased to 65～75 DEG C, drip 70～80mL mass fraction 30% 2 (trichloromethyl) carbonic ester tetrahydrochysene furans
Muttering solution, controlling rate of addition is 1～3mL/min, insulated and stirred reaction 5～6h after completion of dropwise addition, reaction terminate after 800～
It is heated to backflow under 900W microwave power, after backflow 20～30min, is cooled to room temperature；
(3) the above-mentioned there-necked flask being cooled to room temperature is put in oil bath pan, after being warming up to 55～65 DEG C, drip 40～50mL matter
Amount mark 35% methylamine water solution, controlling rate of addition is 2～4mL/min, insulated and stirred reaction 3～5h after dropping, will after reaction
Reactant liquor in flask is poured in separatory funnel, takes upper liquid after stratification, puts into baking oven after being washed with deionized water 3～5 times
In, at a temperature of 50～60 DEG C, it is dried 5～7h, the most i.e. can get 2-amino-N, 5-dimethyl benzamide；
(4) by above-mentioned 2-amino-N, 5-dimethyl benzamide adds in flask, and add 12～15mL glacial acetic acid, 35～
40mL deionized water, drips 35～40mL mass fraction 35% hydrobromic acid solutions in flask, controls to drip after stirring 25～35min
Acceleration is 5～7mL/min, puts in water-bath after completion of dropwise addition after insulated and stirred 20～30min, at a temperature of 35～40 DEG C to
In flask drip 10～12mL mass fraction 30% hydrogen peroxide, control to be added dropwise to complete 10～20min, be warming up to after dropping 50～
60 DEG C, add 35～40mL deionized waters and 1.2～1.5g sodium sulfitees after stirring 1～3h, divide by quality after stirring mixing
Several 30% sodium hydroxide solution regulation pH are 5.5～6.5, filter, obtain filtering residue, after being washed with deionized 3～5 times, put after regulation
Enter and vacuum drying oven is dried at a temperature of 60～80 DEG C 8～10h, i.e. can get the 2-bromo-N of amino-4-, 5-dimethyl phenacyl
Amine solid.
Specific embodiments
A kind of 2-bromo-N of amino-4-that the present invention relates to, the building-up process of 5-dimethyl benzamide comprises the following steps:
First in the four-hole boiling flask of 500mL, it is sequentially added into 120～150mL deionized waters, 20～22g2-nitro-5-methylbenzene
Formic acid, 10～12g sodium hydroxide, 20～22g ferric chloride (FeCl36H2O) and 0.1～0.2g palladium, put into water by four-hole boiling flask after addition
In bath, rise high-temperature and drip 13～15mL mass fraction 60% hydrazine hydrate aqueous solutions to 75～80 DEG C of backward flasks, control to drip
Acceleration is 3～5mL/min, insulated and stirred reaction 5～7h after completion of dropwise addition, and reaction cools down room temperature, by reactant mistake after terminating
Filter to obtain filtrate, and be 7.0 with mass fraction 20% hydrochloric acid regulation filtrate pH, the stirring 60～80min after regulation, sucking filtration after stirring
Filtering residue, and put in baking oven after deionized water rinsing 3～5 times, be dried 6～10h at 60～70 DEG C, dried 2-ammonia
Base-5-ar-Toluic acid；Equipped with agitator, condensing tube, thermometer, constant pressure funnel 500mL four-hole boiling flask in add
Above-mentioned 2-amino-5-ar-Toluic acid solid and 200～250mL dichloromethane and 0.3～0.5mL pyridine, by four mouthfuls after addition
Flask is put in oil bath, drips 70～80mL mass fraction 30% 2 (trichloromethyl) carbon when being increased to 65～75 DEG C in flask
Acid esters tetrahydrofuran solution, controlling rate of addition is 1～3mL/min, insulated and stirred reaction 5～6h after completion of dropwise addition, reaction knot
Under 800～900W microwave powers, it is heated to backflow after bundle, after backflow 20～30min, is cooled to room temperature；It is cooled to room by above-mentioned
The there-necked flask of temperature places in oil bath pan, drips 40～50mL mass fraction 35% methylamine water solutions after being warming up to 55～65 DEG C,
Controlling rate of addition is 2～4mL/min, and after dropping, insulated and stirred reaction 3～5h, pours into the reactant liquor in flask after reaction point
In liquid funnel, after stratification, take upper liquid, put into after being washed with deionized water 3～5 times in baking oven, dry at a temperature of 50～60 DEG C
Dry 5～7h, the most i.e. can get 2-amino-N, 5-dimethyl benzamide；By the above-mentioned 2-amino-N, 5-bis-prepared
Methyl benzamide adds in flask, and adds 12～15mL glacial acetic acid, 35～40mL deionized water, after stirring 25～35min
Dripping 35～40mL mass fraction 35% hydrobromic acid solutions in flask, controlling rate of addition is 5～7mL/min, after completion of dropwise addition
Insulated and stirred 20～30min, puts into after stirring in water-bath and to drip 10～12mL mass at a temperature of 35～40 DEG C in flask and divide
Several 30% hydrogen peroxide, control to be added dropwise to complete 10～20min, are warming up to 50～60 DEG C after dropping, stirring 1～3h after add 35～
40mL deionized water and 1.2～1.5g sodium sulfitees, after stirring mixing with mass fraction 30% sodium hydroxide solution regulation pH be
5.5～6.5, filter after regulation, obtain filtering residue, after being washed with deionized 3～5 times, put in vacuum drying oven at 60～80 DEG C
At a temperature of be dried 8～10h, i.e. can get the 2-bromo-N of amino-4-, 5-dimethyl benzamide solid.
Example 1
First in the four-hole boiling flask of 500mL, it is sequentially added into 120mL deionized water, 20g2-nitro-5-ar-Toluic acid, 10g hydrogen
Sodium oxide, 20g ferric chloride (FeCl36H2O) and 0.1g palladium, put in water-bath by four-hole boiling flask after addition, rises high-temperature to after 75 DEG C
Dripping 13mL mass fraction 60% hydrazine hydrate aqueous solution in flask, control rate of addition is 3mL/min, is incubated after completion of dropwise addition
Stirring reaction 5h, reaction cools down room temperature after terminating, is filtered to get filtrate by reactant, and regulates filtrate with mass fraction 20% hydrochloric acid
PH is 7.0, the stirring 60min after regulation, and after stirring, sucking filtration obtains filtering residue, and puts in baking oven with after deionized water rinsing 3 times,
60 DEG C of dry 6h, dried 2-amino-5-ar-Toluic acid；Equipped with agitator, condensing tube, thermometer, constant pressure addition leakage
The 500mL four-hole boiling flask of bucket adds above-mentioned 2-amino-5-ar-Toluic acid solid and 200mL dichloromethane and 0.3mL pyridine,
After addition, four-hole boiling flask is put in oil bath, in flask, when being increased to 65 DEG C, drip 70mL mass fraction 30% 2 (three chloromethanes
Base) carbonic ester tetrahydrofuran solution, control rate of addition is 1mL/min, and insulated and stirred reaction 5h after completion of dropwise addition, reaction terminates
After be heated under 800W microwave power backflow, backflow 20min after be cooled to room temperature；By the above-mentioned there-necked flask being cooled to room temperature
Placing in oil bath pan, drip 40mL mass fraction 35% methylamine water solution after being warming up to 55 DEG C, control rate of addition is 2mL/
Min, after dropping, insulated and stirred reaction 3h, pours in separatory funnel by the reactant liquor in flask after reaction, takes after stratification
Layer liquid, puts into after being washed with deionized water 3 times in baking oven, is dried 5h, the most i.e. can get 2-amino-N, 5-at a temperature of 50 DEG C
Dimethyl benzamide；By the above-mentioned 2-amino-N prepared, 5-dimethyl benzamide adds in flask, and adds 12mL
Glacial acetic acid, 35mL deionized water, drip 35mL mass fraction 35% hydrobromic acid solution in flask, control dropping after stirring 25min
Speed is 5mL/min, insulated and stirred 20min after completion of dropwise addition, puts in water-bath and drip in flask at a temperature of 35 DEG C after stirring
Add 10mL mass fraction 30% hydrogen peroxide, control to be added dropwise to complete at 10min, after dropping, be warming up to 50 DEG C, after stirring 1h, add 35mL
Deionized water and 1.2g sodium sulfite, regulating pH with mass fraction 30% sodium hydroxide solution after stirring mixing is 5.5, regulation
Rear filtration, obtains filtering residue, after being washed with deionized 3 times, puts into and is dried 8h in vacuum drying oven at a temperature of 60 DEG C, the most available
The bromo-N of 2-amino-4-, 5-dimethyl benzamide solid.
Example 2
First in the four-hole boiling flask of 500mL, it is sequentially added into 135mL deionized water, 21g2-nitro-5-ar-Toluic acid, 11g hydrogen
Sodium oxide, 21g ferric chloride (FeCl36H2O) and 0.15g palladium, put in water-bath by four-hole boiling flask after addition, rises high-temperature to after 77 DEG C
Dripping 14mL mass fraction 60% hydrazine hydrate aqueous solution in flask, control rate of addition is 4mL/min, is incubated after completion of dropwise addition
Stirring reaction 6h, reaction cools down room temperature after terminating, is filtered to get filtrate by reactant, and regulates filtrate with mass fraction 20% hydrochloric acid
PH is 7.0, the stirring 70min after regulation, and after stirring, sucking filtration obtains filtering residue, and puts in baking oven with after deionized water rinsing 4 times,
65 DEG C of dry 8h, dried 2-amino-5-ar-Toluic acid；Equipped with agitator, condensing tube, thermometer, constant pressure addition leakage
The 500mL four-hole boiling flask of bucket adds above-mentioned 2-amino-5-ar-Toluic acid solid and 225mL dichloromethane and 0.4mL pyridine,
After addition, four-hole boiling flask is put in oil bath, in flask, when being increased to 70 DEG C, drip 75mL mass fraction 30% 2 (three chloromethanes
Base) carbonic ester tetrahydrofuran solution, control rate of addition is 2mL/min, insulated and stirred reaction 5.5h after completion of dropwise addition, reaction knot
Under 800～900W microwave powers, it is heated to backflow after bundle, after backflow 25min, is cooled to room temperature；By the above-mentioned room temperature of being cooled to
There-necked flask places in oil bath pan, drips 45mL mass fraction 35% methylamine water solution, control rate of addition after being warming up to 60 DEG C
For 3mL/min, after dropping, insulated and stirred reaction 4h, pours in separatory funnel by the reactant liquor in flask after reaction, stratification
After take upper liquid, put into after being washed with deionized water 3 times in baking oven, at a temperature of 55 DEG C be dried 6h, the most i.e. can get 2-ammonia
Base-N, 5-dimethyl benzamide；By the above-mentioned 2-amino-N prepared, 5-dimethyl benzamide adds in flask, and
Add 13mL glacial acetic acid, 37mL deionized water, in flask, after stirring 30min, drip 37mL mass fraction 35% hydrobromic acid solution,
Control rate of addition is 6mL/min, insulated and stirred 25min after completion of dropwise addition, puts in water-bath 35～40 DEG C of temperature after stirring
Lower dropping 11mL mass fraction 30% hydrogen peroxide in flask, controls to be added dropwise to complete at 15min, is warming up to 55 DEG C after dropping, stirring
Add 37mL deionized water and 1.4g sodium sulfite after 2h, regulate with mass fraction 30% sodium hydroxide solution after stirring mixing
PH is 6.0, filters, obtain filtering residue after regulation, after being washed with deionized 4 times, puts in vacuum drying oven dry at a temperature of 70 DEG C
Dry 9h, i.e. can get the 2-bromo-N of amino-4-, 5-dimethyl benzamide solid.
Example 3
First in the four-hole boiling flask of 500mL, it is sequentially added into 150mL deionized water, 22g2-nitro-5-ar-Toluic acid, 12g hydrogen
Sodium oxide, 22g ferric chloride (FeCl36H2O) and 0.2g palladium, put in water-bath by four-hole boiling flask after addition, rises high-temperature to after 80 DEG C
Dripping 15mL mass fraction 60% hydrazine hydrate aqueous solution in flask, control rate of addition is 5mL/min, is incubated after completion of dropwise addition
Stirring reaction 7h, reaction cools down room temperature after terminating, is filtered to get filtrate by reactant, and regulates filtrate with mass fraction 20% hydrochloric acid
PH is 7.0, the stirring 80min after regulation, and after stirring, sucking filtration obtains filtering residue, and puts into baking oven after deionized water rinsing 3～5 times
In, at 70 DEG C of dry 10h, dried 2-amino-5-ar-Toluic acid；Equipped with agitator, condensing tube, thermometer, constant voltage
The 500mL four-hole boiling flask of Dropping funnel adds above-mentioned 2-amino-5-ar-Toluic acid solid and 250mL dichloromethane and
0.5mL pyridine, puts in oil bath by four-hole boiling flask after addition, drips 80mL mass fraction 30% when being increased to 75 DEG C in flask
Two (trichloromethyl) carbonic ester tetrahydrofuran solution, control rate of addition is 3mL/min, insulated and stirred reaction after completion of dropwise addition
6h, reaction is heated to backflow under 900W microwave power, is cooled to room temperature after backflow 30min after terminating；It is cooled to room by above-mentioned
The there-necked flask of temperature places in oil bath pan, drips 50mL mass fraction 35% methylamine water solution, control dropping after being warming up to 65 DEG C
Speed is 4mL/min, and after dropping, insulated and stirred reaction 5h, pours in separatory funnel by the reactant liquor in flask after reaction, stands
Take upper liquid after layering, put into after being washed with deionized water 5 times in baking oven, at a temperature of 60 DEG C, be dried 7h, the most available
2-amino-N, 5-dimethyl benzamide；By the above-mentioned 2-amino-N prepared, 5-dimethyl benzamide adds flask
In, and add 15mL glacial acetic acid, 40mL deionized water, in flask, drip 40mL mass fraction 35% hydrobromic acid after stirring 35min
Solution, control rate of addition is 7mL/min, insulated and stirred 30min after completion of dropwise addition, puts in water-bath 40 DEG C of temperature after stirring
Lower dropping 12mL mass fraction 30% hydrogen peroxide in flask, controls to be added dropwise to complete 10～20min, is warming up to 60 DEG C after dropping,
40mL deionized water and 1.5g sodium sulfite is added, with mass fraction 30% sodium hydroxide solution after stirring mixing after stirring 3h
Regulation pH is 6.5, filters, obtain filtering residue, after being washed with deionized 5 times, put in vacuum drying oven 80 DEG C of temperature after regulation
Under be dried 10h, i.e. can get the 2-bromo-N of amino-4-, 5-dimethyl benzamide solid.
Claims (1)
1. the bromo-N of 2-amino-4-, the synthetic method of 5-dimethyl benzamide, it is characterised in that the bromo-N of 2-amino-4-, 5-
The synthesis of dimethyl benzamide:
Be sequentially added in the four-hole boiling flask of 500mL 120～150mL deionized waters, 20～22g2-nitro-5-ar-Toluic acid,
10～12g sodium hydroxide, 20～22g ferric chloride (FeCl36H2O) and 0.1～0.2g palladium, put into water-bath by four-hole boiling flask after addition
In, rise high-temperature and drip 13～15mL mass fraction 60% hydrazine hydrate aqueous solutions to 75～80 DEG C of backward flasks, control dropping speed
Degree is 3～5mL/min, insulated and stirred reaction 5～7h after completion of dropwise addition, and reactant is filtered after cooling down room temperature after terminating by reaction
Filtrate, and be 7.0 with mass fraction 20% hydrochloric acid regulation filtrate pH, the stirring 60～80min after regulation, after stirring, sucking filtration must be filtered
Slag, and put in baking oven after deionized water rinsing 3～5 times, is dried 6～10h at 60～70 DEG C, dried 2-amino-5-
Ar-Toluic acid；
Equipped with agitator, condensing tube, thermometer, constant pressure funnel 500mL four-hole boiling flask in add above-mentioned 2-amino-5-
Ar-Toluic acid solid and 200～250mL dichloromethane, 0.3～0.5mL pyridine, put in oil bath by four-hole boiling flask after addition,
In flask, 70～80mL mass fraction 30% 2 (trichloromethyl) carbonic ester oxolanes are dripped molten when being increased to 65～75 DEG C
Liquid, controlling rate of addition is 1～3mL/min, and after completion of dropwise addition, insulated and stirred reaction 5～6h, reacts after terminating 800～900W
It is heated to backflow under microwave power, after backflow 20～30min, is cooled to room temperature；
The above-mentioned there-necked flask being cooled to room temperature is put in oil bath pan, drips 40～50mL mass after being warming up to 55～65 DEG C and divide
Several 35% methylamine water solutions, controlling rate of addition is 2～4mL/min, and insulated and stirred reaction 3～5h after dropping, by flask after reaction
In reactant liquor pour in separatory funnel, take upper liquid after stratification, put into after being washed with deionized water 3～5 times in baking oven,
It is dried 5～7h at a temperature of 50～60 DEG C, the most i.e. can get 2-amino-N, 5-dimethyl benzamide；
By above-mentioned 2-amino-N, 5-dimethyl benzamide adds in flask, and adds 12～15mL glacial acetic acid, 35～40mL
Ionized water, drips 35～40mL mass fraction 35% hydrobromic acid solutions in flask, controls rate of addition after stirring 25～35min
It is 5～7mL/min, puts in water-bath after insulated and stirred 20～30min after completion of dropwise addition, at a temperature of 35～40 DEG C in flask
Dropping 10～12mL mass fraction 30% hydrogen peroxide, control to be added dropwise to complete 10～20min, are warming up to 50～60 DEG C, stir after dropping
35～40mL deionized waters and 1.2～1.5g sodium sulfitees are added, with mass fraction 30% hydrogen after stirring mixing after mixing 1～3h
Sodium hydroxide solution regulation pH is 5.5～6.5, filters, obtain filtering residue, after being washed with deionized 3～5 times, put into vacuum after regulation
Being dried 8～10h in drying baker at a temperature of 60～80 DEG C, i.e. can get the 2-bromo-N of amino-4-, 5-dimethyl benzamide is solid
Body.
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| WO2022232366A1 (en) * | 2021-04-30 | 2022-11-03 | Fmc Corporation | Hydrogenation of nitrobenzoic acid and nitrobenzamide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022232366A1 (en) * | 2021-04-30 | 2022-11-03 | Fmc Corporation | Hydrogenation of nitrobenzoic acid and nitrobenzamide |
| CN115010621A (en) * | 2022-07-21 | 2022-09-06 | 山东百启生物医药有限公司 | Synthetic method of 4-bromo-3-methylbenzonitrile |
| CN115010621B (en) * | 2022-07-21 | 2023-11-03 | 山东百启生物医药有限公司 | Synthesis method of 4-bromo-3-methylbenzonitrile |
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