CN100564359C - A kind of 2, the preparation method of 3-two chloro-5-nitrapyrins - Google Patents
A kind of 2, the preparation method of 3-two chloro-5-nitrapyrins Download PDFInfo
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- CN100564359C CN100564359C CNB2007100427863A CN200710042786A CN100564359C CN 100564359 C CN100564359 C CN 100564359C CN B2007100427863 A CNB2007100427863 A CN B2007100427863A CN 200710042786 A CN200710042786 A CN 200710042786A CN 100564359 C CN100564359 C CN 100564359C
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Abstract
The invention belongs to 2, preparation method's technical field of 3-two chloro-5-nitrapyrins.Of the present invention 2, the preparation method of 3-two chloro-5-nitrapyrins is a raw material with the commercial 2-chloro-of scale cheap and easy to get 5-chloromethylpyridine, in the presence of catalyzer and chlorine etc., temperature of reaction is 100～250 ℃, chlorination Synthetic 2,3-two chloro-5-nitrapyrins.The used catalyst material of the present invention reaches in the world all large-scale commercial and cheap at home and abroad.The inventive method preparation process is simple, the direct Synthetic 2 of single step reaction, 3-two chloro-5-nitrapyrins, and the productive rate height, the utmost point is applicable to large-scale commercial production.
Description
Technical field
The present invention relates to the organic synthesis field, relate to 2 particularly, preparation method's technical field of 3-two chloro-5-nitrapyrins.
Background technology
2,3-two chloro-5-nitrapyrins are a kind of heterocycle intermediates that using value is arranged very much, have been widely used in agricultural chemicals, medicine and field of fine chemical.
Address following synthetic method in the patent documentations such as US4508907, US4555575, GC1599123: with 2-amino-5-picoline is raw material, through steps such as bromo, chloros, Synthetic 2,3-two chloro-5-nitrapyrins, its weak point is: raw materials cost height, post-reaction treatment separating isomerism body difficulty.
Disclose following method among the US4469896: with perhalogeno aldehyde and unsaturated nitrile is raw material, Synthetic 2, and 3-two chloro-5-nitrapyrins, its weak point is: raw material perhalogeno aldehyde is synthetic to exist certain difficulty with separating to purify.
Disclose following method in the document such as US4331811, US4636565: with 2-chloro-5-nitrapyrin is raw material, in the presence of catalyzer and chlorine, the chlorination Synthetic 2,3-two chloro-5-nitrapyrins, its weak point is: when using this method and preparing, need at first synthesis material 2-chloro-5-nitrapyrin, this feedstock production is difficult for.General is that raw material generates 2-chloro-5-nitrapyrin under UV-light or initiator catalysis with 2-chloro-5-chloromethylpyridine all, does not all have shiploads of merchandiseization at present both at home and abroad.
In sum, according to above-mentioned listed method, have following shortcoming: production cost is too high, catalyzer is expensive and raw material is difficult for obtaining, and makes realization of industrialization have many difficulties.
Summary of the invention
The objective of the invention is to obtain a kind of 2, the preparation method of 3-two chloro-5-nitrapyrins, this method is reacted with the industrial raw material of easily buying, technology is simple, easily row, productive rate are high in aftertreatment, the utmost point is applicable to industrialization.
A further object of the present invention is to obtain the purposes of molybdenum catalyzer.
In a first aspect of the present invention, provide a kind of 1. a kind 2, the preparation method of 3-two chloro-5-nitrapyrins, it comprises the steps:
(a) provide 2-chloro-5-chloromethylpyridine,
(b) in the presence of catalyzer, the described 2-chloro-5-chloromethylpyridine of step (a) is carried out chlorination reaction at 100～250 ℃ with chlorination reagent, obtain described 2,3-two chloro-5-nitrapyrins.
In a specific embodiment of the present invention, described catalyzer is molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination.
In a specific embodiment of the present invention, described chlorination reagent is a chlorine.
In a specific embodiment of the present invention, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, MoCl
2O
2, WCl
6Or its combination.
In a specific embodiment of the present invention, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, WCl
6Or its combination.
Preferably, described molybdenum oxide compound is MoO
2, MoO
3Or its combination.
In a specific embodiment of the present invention, described catalyst consumption is 0.1～10 weight %, with the total weight of 2-chloro-5-chloromethylpyridine.
In a specific embodiment of the present invention, described catalyst consumption is 2～5 weight %, with the total weight of 2-chloro-5-chloromethylpyridine.
In a specific embodiment of the present invention, the temperature of reaction of described chlorination reaction is 150～200 ℃.
In a specific embodiment of the present invention, aforesaid method also comprises the steps:
(c) step (b) is obtained 2,3-two chloro-5-nitrapyrins separate, and obtain purified 2,3-two chloro-5-nitrapyrins and the incomplete by product of all the other chlorinations;
The incomplete by product of described all the other chlorinations is proceeded chlorination reaction preparation 2, and 3-two chloro-5-nitrapyrins are up to reaching required transformation efficiency.
Further aspect of the present invention provides a kind of purposes of molybdenum catalyzer, and it is used for the chlorination reaction of catalysis 2-chloro-5-chloromethylpyridine, preparation 2,3-two chloro-5-nitrapyrins.
In a specific embodiment of the present invention, described molybdenum catalyzer is molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination.
In a specific embodiment of the present invention, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, MoCl
2O
2, WCl
6Or its combination.
In a specific embodiment of the present invention, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, WCl
6Or its combination.
Preferably, described molybdenum oxide compound is MoO
2, MoO
3Or its combination.
Embodiment
The inventor is through extensive and deep research, by improving preparation technology, used a kind of low price, the 2-chloro-5-chloromethylpyridine of large-scale commercial all being arranged both at home and abroad is raw material, under catalyzer and chlorine condition, but single step reaction, and directly generate 2,3-two chloro-5-nitrapyrins have replaced the two-step reaction method of prior art.Present method is reacted with the industrial raw material of easily buying, and technology is simple, easily row, the high utmost point of productive rate are applicable to industrialization in aftertreatment.Finished the present invention on this basis.
Below the present invention is further detailed with the different of prior art.
In the prior art, adopt following two-step reaction Synthetic 2 usually, 3-two chloro-5-nitrapyrins:
Step 1: Synthetic 2 under the effect of UV-light-chloro-5-nitrapyrin;
Step 2: sintetics 2 under lewis acidic effect, 3-two chloro-5-nitrapyrins.
Illustrate:
Step 1: UV-light is used to cause free radical reaction, under the chlorine effect chloromethyl is converted into trichloromethyl, final Synthetic 2-chloro-5-nitrapyrin.
Step 2: Lewis acid acts on the pyridine ring, under the chlorine effect H on the pyridine ring is converted into chlorine.
The inventor once attempted above-mentioned two-step reaction is merged, thereby raised the efficiency and save cost, found following problem:
In UV-light, be raw material with 2-chloro-5-chloromethylpyridine, Synthetic 2 under the Lewis acid effect, 3-two chloro-5-nitrapyrins.But generate easily in the reaction process as 2,4-two chloro-5-nitrapyrins, 2,6-two chloro-5-nitrapyrins, 2,3,4-three chloro-5-nitrapyrins, 2,3, by products such as 6-three chloro-5-nitrapyrins, these by products can't carry out circulating reaction continue to obtain of the present invention 2,3-two chloro-5-nitrapyrins, thus influence yield.React infeasible.
The contriver discovers, in two-step reaction, because chloromethyl is different with the orientation effect of trichloromethyl, chloromethyl is positioned 4 and 6 of pyridine ring, and trichloromethyl is positioned 3 of pyridine ring, earlier under the chlorine effect, chloromethyl is converted into trichloromethyl with UV-light, use Lewis acid in the chlorine effect again, orientation effect is good, does not have by product substantially, reaction generates 2,3-two chloro-5-nitrapyrins.And in single step reaction under the orientation effect of chloromethyl, orientation effect is poor, thereby produces the problems referred to above.
Based on above-mentioned discovery, the contriver has adopted following reaction scheme: with 2-chloro-5-chloromethylpyridine is raw material, under catalyzer and chlorine condition, single step reaction, and directly generate 2, and 3-two chloro-5-nitrapyrins, thus the two-step reaction method of prior art replaced.
Dated especially as not having, compound provided by the present invention can be synthetic by marketable material and traditional chemical transform mode.For example, 2-chloro-5-nitrapyrin of the present invention can be synthetic by marketable material and traditional chemical transform mode.
Catalyzer
The preferred molybdenum oxide compound of molybdenum catalyzer of the present invention, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination.
Catalyzer of the present invention can directly adopt described molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination, also described molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination can be loaded on the inert support as activeconstituents.
The valence state of molybdenum oxide compound of the present invention is unrestricted, can be MoO
2, MoO
3, MoO, Mo
2O
5Or its combination.Preferably, described molybdenum oxide compound is MoO
2, MoO
3Or its combination.
The muriatic valence state of molybdenum of the present invention is unrestricted.Preferably, described molybdenum muriate is MoCl
5
The valence state of molybdenum oxychloride of the present invention is unrestricted.Preferably, described molybdenum muriate is MoCl
2O
2
The valence state of tungsten metal chloride of the present invention is unrestricted.Preferably, described tungsten metal chloride is WCl
6
Described inert support is not particularly limited, and only otherwise goal of the invention of the present invention is produced restriction to get final product, for example can be: graphite, aluminum oxide, various carclazyte or molecular sieve or its combination.
Described supported catalyst can adopt the load method preparation, also can adopt direct method preparation in synthetic inert support to contain the material of active ingredient.
In a preference, load method divides following several steps to finish: prepare inert support earlier, then with solution or this inert support of slurry of containing active ingredient precursor (also being molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination), evaporate the inert support that must contain active ingredient behind the part moisture.
Catalyst consumption of the present invention is not particularly limited, and only otherwise goal of the invention of the present invention is produced restriction to get final product, for example is 0.1～10 weight % particularly, and 2～5 weight % preferably are with the total weight of 2-chloro-5-chloromethylpyridine.
Chlorination reaction
Chlorination reagent of the present invention is not particularly limited, only otherwise goal of the invention of the present invention is produced restriction to get final product.For example, described chlorination reagent is a chlorine.
Described chlorination reagent consumption is not particularly limited, only otherwise goal of the invention of the present invention is produced restriction to get final product.For example, in reaction process, feed chlorine until saturated to raw material.
The temperature of reaction of described chlorination reaction of the present invention is 100～250 ℃ a temperature range, and preferably temperature of reaction is 150～200 ℃.
Reaction temperature is spent the low speed of response that influences, when temperature is lower than 100 ℃, raw material can not liquefy fully, and this reaction is difficult to normally advance, and after temperature of reaction is higher than 250 ℃, by product and high-boiling-point impurity that chlorination replaces obviously increase, and influence the selectivity of this reaction, cause that secondary replaces, and the growing amount of increase high boiling product, reduce product yield, temperature of reaction is preferably 100 ℃～250 ℃, wherein more preferably 150 ℃～200 ℃.
Reaction times decides according to concrete reactant, catalyzer and temperature of reaction, is generally about 10-80 hour preferably 10-20 hour.
For preventing overreaction, and cause that secondary replaces, can adopt ordinary method (as gas-chromatography etc.) that the performance level of reaction is carried out tracking monitor.
Target product can adopt methods such as ultimate analysis, ebulliometry or gaseous mass spectrum to detect proof.
Recycle
The part of not complete reaction of the present invention can reclaim carries out circulating reaction, till reaching required productive rate.
Particularly, chlorination reaction of the present invention also comprises the steps:
(c) step (b) is obtained 2,3-two chloro-5-nitrapyrins separate, and obtain purified 2,3-two chloro-5-nitrapyrins and the incomplete by product of all the other chlorinations;
Chlorination reaction is proceeded in described all the other chlorinations by product completely, up to reaching required transformation efficiency.
Because the by product that the reaction conditions that the present invention adopts makes step (b) obtain has been avoided excessive chlorination, so it can easily continue chlorination reaction and obtain 2,3-two chloro-5-nitrapyrins.
Transformation efficiency can adopt ordinary method (as gas-chromatography etc.) that the performance level of reaction is carried out tracking monitor.
Compound provided by the present invention can be synthetic by marketable material and traditional chemical transform mode.
Above-mentioned synthetic method is the synthetic route of part of compounds of the present invention, according to above-mentioned example, those skilled in the art can synthesize other compounds of the present invention by adjusting diverse ways, and perhaps, those skilled in the art can synthesize compound of the present invention according to existing known technology.The synthetic compound can further be further purified by modes such as column chromatography, high performance liquid chromatography or crystallizations.
Particularly for example, adopt conventional post-treating method (extraction, suction filtration, washing, drying, precipitation etc.) after more than reaction is finished.
Synthetic chemistry is transformed, protection functional group methodology (protect or go and protect) is helpful to synthetic application compound, and be technology commonly known in the art, as R.Larock, ComprehensiveOrganic Transformations, VCH Publishers (1989); T.W.Greene and P.G.M.Wuts, Protective Groups in Organic Synthesis, the third edition, John Wiley andSons (1999); L.Fieser and M.Fieser, Fieser and Fieser ' s Reagentsfor Organic Synthesis, John Wiley and Sons (1994); And L.Paquette, etc., Encyclopedia of Reagents for Organic Synthesis has open among the John Wiley andSons (1995).
Other aspects of the present invention are because the disclosure of this paper is conspicuous to those skilled in the art.
Beneficial effect
(1) the used supplementary material of the present invention reaches in the world all large-scale commercial and cheap at home, in the reaction process without any need for organic solvent, can reduce last handling process, and almost do not have side reaction, throughput is big, the reaction conditions gentleness, cost is low, easy advantage such as suitability for industrialized production, the purity of the product that obtains with preparation method of the present invention can reach more than 99.5%, and productive rate reaches 70-90% usually.
(2) preparation method of the present invention reacts with the industrial raw material of easily buying cheap, shiploads of merchandiseization, the supplementary material of present method is cheap and easy to get, technology is simple, single step reaction directly makes target product, aftertreatment easily row, mild condition, environmental pollution are little, can make 2 with higher yields, 3-two chloro-5-nitrapyrins, easily industrialization simultaneously.
(3) in a preferred embodiment of the present invention, having adopted new catalyzer, also is molybdenum oxide catalyst.It is difficult for the moisture absorption hydrolysis, has reduced the extent of corrosion to reaction vessel, and reaction conditions is gentle more, has reached higher yields and has reduced cost, has reduced environmental pollution.
Below in conjunction with specific embodiment, further illustrate the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.The experimental technique of unreceipted actual conditions in the following example usually according to normal condition, for example is " condition in the smooth organic chemistry handbook of Bel Si (Chemical Industry Press, 1996), or the condition of advising according to manufacturer.Ratio and per-cent are based on weight, unless stated otherwise.
Unless otherwise defined or explanation, same meanings of being familiar with of all specialties used herein and scientific words and those skilled in the art.Any in addition method similar or impartial to described content and material all can be applicable in the inventive method.
Embodiment 1
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) MoO
2, stir, at T
In=175 ℃, in above-mentioned solution, feed Cl
2, reaction in 29 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 651g, productive rate 79.7% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 2:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 0.5g (0.1%wt) MoO
2, stir, at T
In=100 ℃, in above-mentioned solution, feed Cl
2, reaction in 80 hours finishes.2,3-two chloro-5-nitrapyrin crude products washing, through PH=8-9, layering, drying, distillation obtains product 93.2g, productive rate 11.4%.
The incomplete product of chlorination of the present invention can reclaim and carry out circulating reaction, till reaching required productive rate.
Embodiment 3:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) MoO
3, stir, at T
In=175 ℃, in above-mentioned solution, feed Cl
2, reaction in 33 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 638.6g, productive rate 78.5% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 4
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 2.5g (0.5%wt) MoCl
5, stir, at T
In=250 ℃, in above-mentioned solution, feed Cl
2, reaction in 72 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 489.6g, productive rate 59.7% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 5:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) MoCl
5, stir, at T
In=175 ℃, in above-mentioned solution, feed Cl
2, reaction in 35 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 683.6g, productive rate 83.6% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 6
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) MoCl
2O
2, stir, at T
In=200 ℃, in above-mentioned solution, feed Cl
2, reaction in 31 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 614.1g, productive rate 75.1% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 7:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) WCl
6, stir, at T
In=175 ℃～185 ℃, in above-mentioned solution, feed Cl
2, reaction in 12 hours finishes.2,3-two chloro-5-nitrapyrin crude products wash through transferring PH=8-9, layering, and drying, distillation obtains product 721g, and productive rate 87.9%, its boiling point b.p. are 104 ℃ (2mmHg).
Embodiment 8:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 10g (2%wt) WCl
6, stir, at T
In=150 ℃, in solution, feed Cl
2, reaction in 45 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 471.6g, productive rate 57.8% through washing, accent PH=8-9, layering, drying, distillation.
Embodiment 9:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 25g (5%wt) WCl
6, stir, at T
In=175 ℃, in above-mentioned solution, feed Cl
2, reaction in 50 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 453.2g, productive rate 55.1% through washing, PH=8-9, layering, drying, distillation.
The incomplete product of chlorination of the present invention can reclaim the chlorination reaction that circulates, till reaching required productive rate.
Embodiment 10:
In being housed, thermometer, prolong and mechanical stirring 1L four-hole bottle drop into 500g (3.08mol) 2-chloro-5-chloromethylpyridine (molecular weight 162g/mol), 15g (3%wt) WCl
6, stir, at T
In=100 ℃, in above-mentioned solution, feed Cl
2, reaction in 48 hours finishes.2,3-two chloro-5-nitrapyrin crude products obtain product 412.6g, productive rate 50.4% through washing, PH=8-9, layering, drying, distillation.
The incomplete product of chlorination of the present invention can reclaim the chlorination reaction that circulates, till reaching required productive rate.
All quote in this application as a reference at all documents that the present invention mentions, just quoted as a reference separately as each piece document.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after having read above-mentioned teachings of the present invention, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Claims (8)
1. one kind 2, the preparation method of 3-two chloro-5-nitrapyrins is characterized in that, comprises the steps:
(a) provide 2-chloro-5-chloromethylpyridine,
(b) in the presence of catalyzer, the described 2-chloro-5-chloromethylpyridine of step (a) is carried out chlorination reaction at 100～250 ℃ with chlorination reagent, obtain described 2,3-two chloro-5-nitrapyrins;
Described catalyzer is molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination;
With described chlorination reagent be chlorine.
2. the method for claim 1 is characterized in that, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, MoCl
2O
2, WCl
6Or its combination.
3. the method for claim 1 is characterized in that, described catalyzer is selected from MoO
2, MoO
3, MoCl
5, WCl
6Or its combination.
4. the method for claim 1 is characterized in that, described catalyst consumption is 0.1～10 weight %, with the total weight of 2-chloro-5-chloromethylpyridine.
5. the method for claim 1 is characterized in that, described catalyst consumption is 2～5 weight %, with the total weight of 2-chloro-5-chloromethylpyridine.
6. the method for claim 1 is characterized in that, the temperature of reaction of described chlorination reaction is 150～200 ℃.
7. as each described method of claim 1～6, it is characterized in that, also comprise the steps:
(c) step (b) is obtained 2,3-two chloro-5-nitrapyrins separate, and obtain purified 2,3-two chloro-5-nitrapyrins and the incomplete by product of all the other chlorinations;
The incomplete by product of described all the other chlorinations is proceeded chlorination reaction preparation 2, and 3-two chloro-5-nitrapyrins are up to reaching required transformation efficiency.
8. the purposes of a molybdenum catalyzer is characterized in that, is used for the chlorination reaction of catalysis 2-chloro-5-chloromethylpyridine, preparation 2,3-two chloro-5-nitrapyrins;
Described molybdenum catalyzer is molybdenum oxide compound, molybdenum muriate, molybdenum oxychloride, tungsten metal chloride or its combination.
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| CN104557683B (en) * | 2013-10-09 | 2016-11-02 | 李波 | The preparation method of 2,3-bis-chloro-5-trifluoromethylpyridines |
| CN103787961A (en) * | 2014-03-07 | 2014-05-14 | 江苏省激素研究所股份有限公司 | Efficient haloxyfop-methyl synthesizing method |
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