CN109879818A - The synthetic method of N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide - Google Patents
The synthetic method of N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide Download PDFInfo
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- CN109879818A CN109879818A CN201910271806.7A CN201910271806A CN109879818A CN 109879818 A CN109879818 A CN 109879818A CN 201910271806 A CN201910271806 A CN 201910271806A CN 109879818 A CN109879818 A CN 109879818A
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- dimethoxypyridin
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- methylsulfonyl
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Abstract
The present invention provides N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide synthetic method, it is in a solvent, 2- nitryl-4-thiamphenicol benzoic acid and 2- amino -4 is added, 6- dimethoxypyridin, in the presence of catalyst and auxiliary agent, stirring is lower and is warming up to micro- reflux, condensation reaction obtains N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide.Synthetic method of the present invention is easy to operate, and preparation process technique is relatively easy to control, and reduces pollutant kind, so being environmentally protective process route.
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to a kind of N- (4,6- dimethoxypyridin -2- base) -4- first
The synthetic method of sulfuryl -2- nitrobenzamide.
Background technique
Mesotrione is by a kind of weeding of inhibition p-hydroxyphenypyruvate dioxydenase of Syngenta Co., Ltd's exploitation
Agent.We are when modifying its molecular structure, with the key intermediate 2- nitryl-4-thiamphenicol benzoic acid of mesotrione
Condensation reaction is carried out with 2- amino-4,6-dimethoxy pyrimidine, is meaningfully composite N- (4,6- dimethoxypyridin -2- base) -
This substance of 4- methylsulfonyl -2- nitrobenzamide.Usually this kind of reaction is first to be prepared into 2- nitryl-4-thiamphenicol benzoic acid
Acyl chlorides, then condensation reaction is carried out with 2- amino-4,6-dimethoxy pyrimidine, but author does not obtain being wanted with this method
Target compound.Therefore we look for another way, and 2- nitryl-4-thiamphenicol benzoic acid and 2- amino -4,6- dimethoxy is phonetic
Pyridine, in the presence of catalyst and auxiliary agent, directly progress condensation reaction, to prepare target compound N- (4,6- dimethoxies
Yl pyrimidines -2- base) -4- methylsulfonyl -2- nitrobenzamide.Have no that document discloses the synthetic method for reporting the substance at present.
Summary of the invention
The purpose of the present invention is to provide a kind of synthesis N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitre
The synthetic method of yl-benzamide.
Its technical solution is as follows:
The synthetic method of N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide is added in a solvent
2- nitryl-4-thiamphenicol benzoic acid and 2- amino-4,6-dimethoxy pyrimidine, in the presence of catalyst and auxiliary agent, under stirring simultaneously
It is warming up to micro- reflux, condensation reaction obtains N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide.
Further scheme, the catalyst are three fluoboric acid, and additional amount and 2- nitryl-4-thiamphenicol benzoic acid are added
Amount mass ratio is 0.05-0.2:13.
Further scheme, the auxiliary agent are n,N-Dimethylformamide, and solvent is trimethylbenzene；The solvent and auxiliary agent
Volume ratio is 250:5-15.Auxiliary agent mainly plays hydrotropy.
Further scheme is down to room temperature after the condensation reaction, carries out first time filtering to reactant；In filter cake
Middle addition ethyl alcohol and the stirring extremely reflux that heats up, then carry out filtering for second while hot；Second of filtered filtrate is carried out cold
But it crystallizes, carries out third time filtering again after material is sufficiently precipitated, gained filter cake dries to obtain N- (4,6- dimethoxypyridin -2-
Base) -4- methylsulfonyl -2- nitrobenzamide.
Further scheme, the condensation reaction are carried out in the reactor of belt stirrer and condenser pipe.
The present invention is directly by 2- nitryl-4-thiamphenicol benzoic acid and 2- amino -4,6- dimethoxypyridin condensation reaction system
Standby to obtain N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide, synthetic method is easy to operate, and makes
Standby process is relatively easy to control, and reduces pollutant kind, so being environmentally protective process route.
Specific embodiment
The method of the invention is described in detail below with reference to specific embodiment
Embodiment 1:
By 13 grams of 2- nitryl-4-thiamphenicol benzoic acids, 8 grams of 2- amino -4,6- dimethoxypyridin investment belt stirrers and condensation
In 250 milliliters of trimethylbenzenes in the three-necked flask of pipe, 0.10 gram of three fluoboric acid is added, n,N-Dimethylformamide 5ml is being stirred
It descends and is warming up to micro- reflux.It samples gas and composes middle control analysis, to reactant concentration less than 0.5%, stop reaction and be down to room temperature, go forward side by side
Ethyl alcohol is added in row filtering, filter cake, is warming up to reflux, and reflux after five minutes, is filtered, filtrate crystallisation by cooling while hot, sufficiently analysed to material
Refiltered after out, filter cake dries to obtain target compound, and content 99.7%(gas composes normalization method), yield 67.1%.
Embodiment 2:
By 13 grams of 2- nitryl-4-thiamphenicol benzoic acids, 8 grams of 2- amino -4,6- dimethoxypyridin investment belt stirrers and condensation
250 milliliters of trimethylbenzenes in the three-necked flask of pipe are added 0.15 gram, n,N-Dimethylformamide 5ml of three fluoboric acid, under stiring
And it is warming up to micro- reflux.It samples gas and composes middle control analysis, to reactant concentration less than 0.5%, stop reaction and be down to room temperature, and carry out
Methanol is added in filtering, filter cake, is warming up to reflux, and reflux after five minutes, is filtered, filtrate crystallisation by cooling while hot, is sufficiently precipitated to material
After refilter, filter cake dries to obtain target compound, and content 99.4%(gas composes normalization method), yield 67.2%.
Embodiment 3:
By 13 grams of 2- nitryl-4-thiamphenicol benzoic acids, 8 grams of 2- amino -4,6- dimethoxypyridin investment belt stirrers and condensation
In 250 milliliters of trimethylbenzenes in the three-necked flask of pipe, 0.1 gram of three fluoboric acid is added, n,N-Dimethylformamide 10ml is being stirred
It descends and is warming up to micro- reflux.It samples gas and composes middle control analysis, to reactant concentration less than 0.5%, stop reaction and be down to room temperature, go forward side by side
Methanol is added in row filtering, filter cake, is warming up to reflux, and reflux after five minutes, is filtered, filtrate crystallisation by cooling while hot, sufficiently analysed to material
Refiltered after out, filter cake dries to obtain target compound, and content 99.6%(gas composes normalization method), yield 67.3%.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (5)
- The synthetic method of 1.N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide, it is characterised in that: In a solvent, 2- nitryl-4-thiamphenicol benzoic acid and 2- amino-4,6-dimethoxy pyrimidine is added, is deposited in catalyst and auxiliary agent Under, stirring is lower and is warming up to micro- reflux, and condensation reaction obtains N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitro Benzamide.
- 2. synthetic method according to claim 1, it is characterised in that: the catalyst is three fluoboric acid, additional amount It is 0.05-0.2:13 with 2- nitryl-4-thiamphenicol benzoic acid additional amount mass ratio.
- 3. synthetic method according to claim 1, it is characterised in that: the auxiliary agent is n,N-Dimethylformamide, molten Agent is trimethylbenzene；The volume ratio of the solvent and auxiliary agent is 250:5-15.
- 4. synthetic method according to claim 1, it is characterised in that: after the condensation reaction, room temperature is down to, to anti- Object is answered to carry out first time filtering；Ethyl alcohol is added in filter cake and the stirring that heats up is to flowing back, then carries out filtering for second while hot；It is right Second of filtered filtrate carries out crystallisation by cooling, carries out third time filtering, the drying of gained filter cake again after material is sufficiently precipitated Obtain N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide.
- 5. synthetic method according to claim 1, it is characterised in that: the condensation reaction is with blender and condensation It is carried out in the reactor of pipe.
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| CN201910271806.7A CN109879818A (en) | 2019-04-04 | 2019-04-04 | The synthetic method of N- (4,6- dimethoxypyridin -2- base) -4- methylsulfonyl -2- nitrobenzamide |
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Citations (4)
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| CN1680342A (en) * | 2005-01-19 | 2005-10-12 | 南开大学 | Benzothiadiazole derivatives and their synthesis methods and screening of induced disease resistance activity |
| CN101492416A (en) * | 2001-08-17 | 2009-07-29 | 阿斯特拉曾尼卡有限公司 | Compounds effecting glucokinase |
| CN102015660A (en) * | 2008-04-23 | 2011-04-13 | 协和发酵麒麟株式会社 | 2-aminoquinazoline derivative |
| CN106459072A (en) * | 2014-03-20 | 2017-02-22 | 拜耳制药股份公司 | Inhibitors of the Wnt signaling pathway |
-
2019
- 2019-04-04 CN CN201910271806.7A patent/CN109879818A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101492416A (en) * | 2001-08-17 | 2009-07-29 | 阿斯特拉曾尼卡有限公司 | Compounds effecting glucokinase |
| CN1680342A (en) * | 2005-01-19 | 2005-10-12 | 南开大学 | Benzothiadiazole derivatives and their synthesis methods and screening of induced disease resistance activity |
| CN102015660A (en) * | 2008-04-23 | 2011-04-13 | 协和发酵麒麟株式会社 | 2-aminoquinazoline derivative |
| CN106459072A (en) * | 2014-03-20 | 2017-02-22 | 拜耳制药股份公司 | Inhibitors of the Wnt signaling pathway |
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Application publication date: 20190614 |
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