CN106380427A - Synthesis method of N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide - Google Patents
Synthesis method of N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide Download PDFInfo
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- CN106380427A CN106380427A CN201610763679.9A CN201610763679A CN106380427A CN 106380427 A CN106380427 A CN 106380427A CN 201610763679 A CN201610763679 A CN 201610763679A CN 106380427 A CN106380427 A CN 106380427A
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- sulfonyl
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- anisoyl
- cyclopropyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
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Abstract
The invention relates to a synthesis method of N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide. The method comprises that 4-carboxybenzenesulfonamide as a raw material undergoes a reaction in the presence of an acid as a catalyst to produce N-cyclopropyl-[[(2-methoxybenzoyl)amino]sulfonyl]benzamide. A high efficiency catalyst reduces a chlorination reagent use amount by 40%, discharge of acidic gas such as sulfur dioxide and hydrogen chloride is greatly reduced, technical requirements of energy saving, consumption reduction and environmental protection are satisfied, a product yield is high, product purity is high, and the synthesis method has advantages in cost and quality and has a large development space in industrial production.
Description
Technical field
The present invention relates to chemical field is and in particular to a kind of N- cyclopropyl-[[(2- anisoyl) amino] sulphonyl
Base] Benzoylamide synthetic method.
Background technology
N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide, English name
Cyprosulfamide, molecular formula：C18H18N2O5S, molecular weight 374.41, structural formula is as follows：
N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide is that Beyer Co., Ltd was sent out in 1997
A kind of existing acylsulfamoylbenzamides compound.As a kind of safener of herbicide, since two thousand eight, every year with two
The rate of increase of digit increases so as to more than 65 kind of grassy weed and broad leaved weed can effectively be prevented and kill off, such as wild broomcorn millet, Herba Digitariae, Amaranthus retroflexus,
Herba Setariae Viridis, Herba Eleusines Indicae, Herba chenopodii, barnyard grass and Herba Abutili etc..
United States Patent (USP) (WO9916744) describes acylsulfamoylbenzamides derivant and its is used for removing as safener
Control the purposes of weeds, this safe Herbicidal mixture has ideal agronomy performance and has potential business in careless agent
It is worth.Chinese patent CN100413848 reports to its synthetic method, but chloroform is used as reaction dissolvent poor selectivity,
Purity is low, and chlorination reagent amount ratio is larger, complex process, and the response time is long, also can produce sour gas sulfur dioxide and chlorination
Hydrogen, etching apparatus, contaminated air, it is unfavorable for popularization and application.Reaction temperature is higher, and it is expensive, not environmentally, uneconomical.
For these reasons, develop a kind of N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] benzoyl
The green syt new method of amine is imperative.
Content of the invention
For overcoming the defect of prior art, the purpose of the present invention is exactly to provide a kind of economical synthesis N- cyclopropyl-[[(2-
Anisoyl) amino] sulfonyl] and Benzoylamide method, can effectively solving under low expense, using selectivity high,
The strong catalyst of repeatability is referred to as economical synthesis N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl]
Benzoylamide, its process route is simple, the response time is short, its thionyl chloride decrement 40%, and greatly reduces sour gas dioxy
Change the discharge of sulfur and hydrogen chloride.
The present invention, using P-Carboxybenzenesulfonamide as raw material, using acid as catalyst, prepares N- cyclopropyl-[[(2- first
Epoxide benzoyl) amino] sulfonyl] Benzoylamide, synthetic route is：
Comprise the following steps that：
(1) put into o-methoxybenzoic acid, P-Carboxybenzenesulfonamide, catalyst in toluene solvant, rise temperate zone water to clear
Bright；
(2), after system is limpid, it is cooled to 40-50 DEG C, Deca thionyl chloride, it is warming up to backflow, be incubated 1-5 hour, reaction
Desolvation after end；
(3) material after above-mentioned desolvation is added dichloromethane, be added drop-wise to cyclopropylamine with sodium hydrate aqueous solution pair
Dichloromethane solution in, -10 DEG C -0 DEG C of controlling reaction temperature carries out reacting 5-10 hour, and sucking filtration obtains filter cake, and filter cake is N-
Cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide.
Select toluene as reaction dissolvent in step (1), not only boiling point is high, and can carry water, this reaction O-methoxy
Benzoic acid, P-Carboxybenzenesulfonamide, under catalysts conditions, select toluene temperature rising reflux band water, water byproduct are taken out of, promotes
Balance is moved rearwards by, thus improving reaction efficiency.Response time is 1-1.5h.P-Carboxybenzenesulfonamide and o-methoxybenzoic acid
Mol ratio is 1:During 1.1-1.2, preferable reaction effect can be obtained.
After the completion of dividing water reaction, add thionyl chloride in reaction system, thionyl chloride is rubbed with P-Carboxybenzenesulfonamide
That ratio is 1:1.1-1.6.Deca thionyl chloride temperature can not be too high, because pressure can be played, the more raised pressure of temperature is about big, has certain
Dangerous；Dropping temperature is less than 40 DEG C, and temperature is too low, and reactivity is low, has unreacted thionyl chloride in a large number in system, after
Temperature of continuing rising, easy slug, and it is unfavorable for follow-up temperature reaction.Completion of dropping, is warming up to backflow, is incubated 3-5 hour, during insulation
Between determined according to reaction result, insulation starts after 3 hours to sample, once o-methoxybenzoic acid, to carboxyl this sulfonamide raw material
Remaining ＜ 0.5%, post processing immediately, if continue insulation backflow material can decompose, insulation is less than 3 hours, cannot react completely,
Impact yield, content.Reaction terminates rear desolvation.
Because the product of o-methoxybenzoic acid, P-Carboxybenzenesulfonamide can preferably be dissolved by dichloromethane, therefore,
Dichloromethane is adopted as solvent in step (3).
It is a class acyl chlorides because o-methoxybenzoic acid and P-Carboxybenzenesulfonamide react the product generating, double Deca are not only
Itself and cyclopropylamine is promoted to react generation N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide, and
Avoid its hydrolysis.- 10 DEG C -0 DEG C of controlling reaction temperature.Reaction temperature is less than -10 DEG C, and whether this reaction or not.Temperature is higher than 0 DEG C,
Hydrolysis impurity can increase to 2%, impact yield, product content.Carry out reacting 5-10 hour, the filter cake that sucking filtration obtains.Step (3)
In, with the molar ratio computing of pure material, sodium hydroxide is 1 with the mol ratio of P-Carboxybenzenesulfonamide:During 1.1-1.8 it is ensured that
Reaction is preferably carried out.In addition, sodium hydrate aqueous solution mass fraction is 15%-30%, both played the effect tiing up acid, avoided again
Product hydrolyzes under conditions of alkalescence is too strong.Sodium hydrate aqueous solution mass fraction preferably 30%.
In the present invention, cyclopropylamine is 1 with the mol ratio of P-Carboxybenzenesulfonamide:2-7.
Catalyst of the present invention is p-methyl benzenesulfonic acid or benzenesulfonic acid or p-nitrophenyl sulfonic acid or its mixture.Due to neighbour
Methoxybenzoic acid, P-Carboxybenzenesulfonamide are in catalyst (p-methyl benzenesulfonic acid or benzenesulfonic acid or p-nitrophenyl sulfonic acid), toluene body
System rises temperate zone water reaction, promotes o-methoxybenzoic acid and P-Carboxybenzenesulfonamide that intermolecular dehydration occurs first, generates sulphur
Uride, is inherently avoided o-methoxybenzoic acid first to be reacted with thionyl chloride and is prepared into o-methoxy benzoyl chloride and to carboxyl
Benzsulfamide is condensed, thus saving the consumption of thionyl chloride.The consumption of described catalyst is P-Carboxybenzenesulfonamide quality
0.5%-15%.
The present invention reduces the consumption of chlorination reagent 40% from effective catalyst, greatly reduces sour gas sulfur dioxide
With the discharge of hydrogen chloride, meet the technological requirement of current energy-conservation, consumption reduction, environmental protection, and product yield is high, purity is high, has into
This advantage, quality-advantage, this synthesis technique has very big development space in the industrial production.
Brief description
Fig. 1 is N- cyclopropyl of the present invention-[[(2- anisoyl) amino] sulfonyl] Benzoylamide nuclear magnetic spectrogram.
Specific embodiment
Below in conjunction with specific embodiment, technical scheme is elaborated, but protection domain is not limited by this.
Embodiment 1
203.22g P-Carboxybenzenesulfonamide (1mol), 167.33g o-methoxybenzoic acid is added in four-hole bottle
(1.1mol), 1.1g p-methyl benzenesulfonic acid stirs 0.5 hour in 600g toluene solvant, and temperature rising reflux reacts 4 hours to limpid；
It is cooled to 40 DEG C, 180g thionyl chloride, to Deca in bottle, after completion of dropping, is incubated 3 hours.Slough solvent, add
The infiltration of 650g dichloromethane obtains the dichloromethane solution of 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride..
Dichloromethane (70g), 74.8g cyclopropylamine (1.3mol), -8 DEG C of temperature control, stirring is added in other four-hole bottle
Under, the dichloromethane solution of 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. is water-soluble with 200g sodium hydroxide
Liquid (mass fraction 30%) double Deca in system.In -4 DEG C of insulations of temperature 9 hours after completion of dropping, -2 DEG C of sucking filtration obtain white
Crystal, content 98.3%, total recovery 93%.
Embodiment 2
101.1g P-Carboxybenzenesulfonamide (0.5mol content 99%200.19), 86g O-methoxy is added in four-hole bottle
Benzoic acid (0.56mol 152.12), 1g benzenesulfonic acid stir 1 hour in 250g toluene solvant, and temperature rising reflux reacts 6 hours extremely
Limpid；
It is cooled to 45 DEG C, to Deca in bottle, after completion of dropping, insulation 4 is little for 78.1g thionyl chloride (1.3eq 118.98)
When.Slough solvent, add the infiltration of 300g dichloromethane to obtain 4- [[(2- anisoyl) amino] sulfonyl] benzoyl
The dichloromethane solution of chlorine.
Dichloromethane (40g), 30.2g cyclopropylamine (1.05eq), -5 DEG C of temperature control, stirring is added in other four-hole bottle
Under, the dichloromethane solution of 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. is water-soluble with 120g sodium hydroxide
Liquid (mass fraction 30%) double Deca in system.In -7 DEG C of insulations of temperature 6 hours after completion of dropping, -2 DEG C of sucking filtration obtain white
Crystal, content 98.1%, total recovery 92.9%.
Embodiment 3
2235g P-Carboxybenzenesulfonamide (11mol, content 99%), 1506g o-methoxybenzoic acid is added in four-hole bottle
(content 99%, 10mol), 335g p-nitrophenyl sulfonic acid stir 1 hour in 4500g toluene solvant, and temperature rising reflux reacts 3 hours
Extremely limpid；
It is cooled to 50 DEG C, 1562g thionyl chloride, to Deca in bottle, after completion of dropping, is incubated 5 hours.Slough solvent, add
The dichloromethane that the infiltration of 3000g dichloromethane obtains 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. is molten
Liquid.
Addition dichloromethane (4000g), 806g cyclopropylamine in other four-hole bottle, -6 DEG C of temperature control, under stirring, 4-
The dichloromethane solution of [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. and 1860g sodium hydrate aqueous solution
(mass fraction 30%) double Deca in system.In -5 DEG C of insulations of temperature 5 hours after completion of dropping, -3 DEG C of sucking filtration obtain white crystalline substance
Body, content 98.9%, total recovery 93.9%.
Embodiment 4
1067g P-Carboxybenzenesulfonamide (5.25mol, content 99%), 768.3g O-methoxy benzene is added in four-hole bottle
Formic acid (content 99%, 5mol), 20g p-nitrophenyl sulfonic acid, 25g p-methyl benzenesulfonic acid, stirs 0.5 in 3000g toluene solvant
Hour, temperature rising reflux reacts 4 hours to limpid；
It is cooled to 50 DEG C, 661g thionyl chloride, to Deca in bottle, after completion of dropping, is incubated 1 hour.Slough solvent, add
The dichloromethane that the infiltration of 1000g dichloromethane obtains 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. is molten
Liquid.
Addition dichloromethane (1000g), 345g cyclopropylamine in other four-hole bottle, -4 DEG C of temperature control, under stirring, 4-
The dichloromethane solution of [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. and 800g sodium hydrate aqueous solution (matter
Amount fraction 30%) double Deca in system.In 0 DEG C of insulation of temperature 10 hours after completion of dropping, -4 DEG C of sucking filtration obtain white crystal,
Content 99.0%, total recovery 92.3%.
Embodiment 5
439.0g P-Carboxybenzenesulfonamide (2.16mol, content 99%), 307.3g O-methoxy benzene is added in four-hole bottle
Formic acid (content 99%, 2mol), 4g benzenesulfonic acid, 4g p-methyl benzenesulfonic acid, stirs 0.5 hour in 800g toluene solvant, heats up
Back flow reaction 3.5 hours is to limpid；
It is cooled to 40 DEG C, 276.4g thionyl chloride, to Deca in bottle, after completion of dropping, is incubated 2.5 hours.Slough solvent,
The infiltration of 600g dichloromethane is added to obtain the dichloromethane of 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride.
Solution.
Addition dichloromethane (600g), 144g cyclopropylamine in other four-hole bottle, -5 DEG C of temperature control, under stirring, 4-
The dichloromethane solution of [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. and 333g sodium hydrate aqueous solution (matter
Amount fraction 30%) double Deca in system.In -10 DEG C of insulations of temperature 10 hours after completion of dropping, -4 DEG C of sucking filtration obtain white crystalline substance
Body, content 98.8%, total recovery 92.1%.
Embodiment 6
11380g P-Carboxybenzenesulfonamide (56mol, content 99%), 8604.7g O-methoxy benzene is added in four-hole bottle
Formic acid (content 99%, 56mol), 300g benzenesulfonic acid, 300g p-methyl benzenesulfonic acid, 300 p-nitrophenyl sulfonic acid are in 80000g toluene
Stir 1 hour in solvent, temperature rising reflux reacts 3 hours to limpid；
It is cooled to 45 DEG C, 7211g thionyl chloride, to Deca in bottle, after completion of dropping, is incubated 2 hours.Slough solvent, add
The dichloromethane that the infiltration of 60000g dichloromethane obtains 4- [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. is molten
Liquid.
Addition dichloromethane (60000g), 3742g cyclopropylamine in other four-hole bottle, -5 DEG C of temperature control, under stirring, 4-
The dichloromethane solution of [[(2- anisoyl) amino] sulfonyl] Benzenecarbonyl chloride. and 8667g sodium hydrate aqueous solution
(mass fraction 30%) double Deca in system.In -4 DEG C of insulations of temperature 8 hours after completion of dropping, -4 DEG C of sucking filtration obtain white crystalline substance
Body, content 98.9%, total recovery 93.0%.
The above, be only presently preferred embodiments of the present invention, and not technical scheme is done with any form
Restriction.Any simple modification, equivalent variations and modification that every technical spirit according to the present invention is made to above case study on implementation,
Each fall within protection scope of the present invention.
Claims (8)
1. the synthetic method of a kind of N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide, its feature
It is, using P-Carboxybenzenesulfonamide as raw material, using acid as catalyst, prepare N- cyclopropyl-[[(2- methoxybenzoyl
Base) amino] sulfonyl] Benzoylamide, comprise the following steps that：
(1) put into o-methoxybenzoic acid, P-Carboxybenzenesulfonamide, catalyst in toluene solvant, rise temperate zone water extremely limpid；
(2), after system is limpid, it is cooled to 40-50 DEG C, Deca thionyl chloride, drips and finishes, be incubated 1-5 hour, reaction removes after terminating
Solvent；
(3) material after above-mentioned desolvation is added dichloromethane, be added drop-wise to the two of cyclopropylamine with sodium hydrate aqueous solution pair
In chloromethanes solution, completion of dropping, -10 DEG C -0 DEG C of controlling reaction temperature carries out reacting 5-10 hour, and sucking filtration obtains filter cake, and filter cake is
For N- cyclopropyl-[[(2- anisoyl) amino] sulfonyl] Benzoylamide.
2. a kind of N- cyclopropyl according to claim 1-[[(2- anisoyl) amino] sulfonyl] benzoyl
The synthetic method of amine is it is characterised in that described catalyst is p-methyl benzenesulfonic acid or benzenesulfonic acid or p-nitrophenyl sulfonic acid or it is mixed
Compound.
3. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide is it is characterised in that the consumption of described catalyst is the 0.5%-15% of P-Carboxybenzenesulfonamide quality.
4. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide is it is characterised in that P-Carboxybenzenesulfonamide and o-methoxybenzoic acid mol ratio are 1:0.9-1.2.
5. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide is it is characterised in that thionyl chloride is 1.1-1.6 with the mol ratio of P-Carboxybenzenesulfonamide:1.
6. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide it is characterised in that with the molar ratio computing of pure material, the mol ratio of sodium hydroxide and P-Carboxybenzenesulfonamide
For 1.1-1.8：1.
7. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide is it is characterised in that with the molar ratio computing of pure material, sodium hydrate aqueous solution mass fraction is 15%-
30%.
8. a kind of N- cyclopropyl according to claim 1 and 2-[[(2- anisoyl) amino] sulfonyl] benzene first
The synthetic method of amide is it is characterised in that cyclopropylamine is 1.05-1.3 with the mol ratio of P-Carboxybenzenesulfonamide:1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111517996A (en) * | 2020-06-11 | 2020-08-11 | 河北兰升生物科技有限公司 | Preparation method and preparation intermediate of benzoyl sulfamoyl benzamide |
| CN113372245A (en) * | 2021-06-17 | 2021-09-10 | 仪征市海帆化工有限公司 | Synthesis method of N-benzoyl-O, O-p-toluenesulfonyl-diethanolamine |
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| CN1272106A (en) * | 1997-09-29 | 2000-11-01 | 阿温提斯作物科学有限公司 | Acylsulfamoyl benzoic acid amides, plant protection agents containing same, and method for producing same |
| CN105636942A (en) * | 2013-10-10 | 2016-06-01 | 拜耳作物科学股份公司 | Process for preparing 4-[[(benzoyl)amino]sulphonyl]benzoyl chlorides and preparation of acylsulphamoylbenzamides |
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2016
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| CN1272106A (en) * | 1997-09-29 | 2000-11-01 | 阿温提斯作物科学有限公司 | Acylsulfamoyl benzoic acid amides, plant protection agents containing same, and method for producing same |
| CN105636942A (en) * | 2013-10-10 | 2016-06-01 | 拜耳作物科学股份公司 | Process for preparing 4-[[(benzoyl)amino]sulphonyl]benzoyl chlorides and preparation of acylsulphamoylbenzamides |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111517996A (en) * | 2020-06-11 | 2020-08-11 | 河北兰升生物科技有限公司 | Preparation method and preparation intermediate of benzoyl sulfamoyl benzamide |
| CN111517996B (en) * | 2020-06-11 | 2023-08-15 | 河北兰升生物科技有限公司 | Preparation method and preparation intermediate of benzoyl sulfamoyl benzamide |
| CN113372245A (en) * | 2021-06-17 | 2021-09-10 | 仪征市海帆化工有限公司 | Synthesis method of N-benzoyl-O, O-p-toluenesulfonyl-diethanolamine |
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