CN104610091B - A kind of method purifying N-toluyl crude formamide - Google Patents
A kind of method purifying N-toluyl crude formamide Download PDFInfo
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Abstract
The present invention relates to organic synthesis field, disclose a kind of method purifying N toluyl crude formamide, the method includes: under solution condition, with acidic materials, N toluyl crude formamide is carried out first and contacts.The N toluyl Methanamide of solid state that can conveniently be preserved by the above-mentioned method of purification using the present invention, and, it is thus achieved that the N toluyl Methanamide good stability of solid state, be conducive to long-term preservation.The above-mentioned method of purification technique of the present invention is simple, be suitable for industrialized great production, and the product obtained by the method for purification of the present invention also has the advantage that yield is high and purity is high.
Description
Technical field
The present invention relates to a kind of method purifying N-toluyl crude formamide.
Background technology
N-toluyl Methanamide is light yellow or white solid, and fusing point is 74 DEG C, is a kind of important
Pesticide intermediate, as described in CN1169989A N-toluyl Methanamide may be used for preparation
Dithiocarbonimide derivatives, N-toluyl Methanamide can be used described in CN102341378A
In preparation 1-alkyl-5-benzoyl-1H-TETRAZOLE derivant, CN102725270A describes N-methylbenzene
Formyl Methanamide may be used for preparing antibacterial.
The carbamate sterilization of N-toluyl Methanamide Ye Shi Tso Tat Co., Ltd., Japan exploitation
The important intermediate of agent picarbutrazox.Its preparation method substantially has following three kinds:
1) document Journal of the American Chemical Society, 132 (21), 7266-7267；
Disclosed in 2010:
But, the defect that this method has step length, yield is low, and benzoyl Methanamide directly with
The selectivity of methylating reagent reaction is bad, easily produces dibasic by-product.
2) disclosed in WO9950231A1 and US5387714A:
This method reactions steps is short, and the yield of three steps is about 75%.But, above-mentioned reaction condition
More harsh, Grignard reagent to be used, and also oxolane reclaims difficulty.The product obtained is solution shape
State, and typically require and be saved in methanol equal solvent.And, the N-methylbenzene of this kind of solution state
Formyl Methanamide is difficult to stable preservation, is also readily generated by-product even preserving in the solution such as methanol
Thing.
3) disclosed in WO2010103783A1:
The method is simple and easy to do, but the product obtained is still solution state, and typically requires preservation
In methanol equal solvent.And, the N-toluyl Methanamide of this kind of solution state is difficult to stable guarantor
Depositing, being also readily generated by-product even preserving in the solution such as methanol.
In sum, prior art exists at 3 not in the method preparing N-toluyl Methanamide
Foot: 1, technique is more complicated, and industrialization difficulty is bigger；2, product yield is relatively low, and purity is low；3,
To product be that solution state is difficult to preserve, it is impossible to obtain the solid product of high-load.
Summary of the invention
It is an object of the invention to overcome and use method disclosed in prior art to produce the N-methylbenzene first obtained
Acyl Methanamide only solution state exist and poor stability and cause be difficult to preserve defect, it is desirable to obtain
A kind of N-toluyl Methanamide of the solid state of convenient preservation and good stability, the therefore present invention
A kind of method purifying N-toluyl crude formamide is provided, is obtained by the method for purification of the present invention
The N-toluyl Methanamide obtained is convenient to be preserved and good stability.
To achieve these goals, the present invention provides a kind of N-toluyl crude formamide of purifying
Method, the method includes: under solution condition, by N-toluyl crude formamide and acid
Matter carries out the first contact.
By the N-first of the solid state that the above-mentioned method of purification using the present invention can conveniently be preserved
Base benzoyl Methanamide, and, it is thus achieved that the N-toluyl Methanamide good stability of solid state,
Be conducive to long-term preservation.The above-mentioned method of purification technique of the present invention is simple, be suitable for industrialized great production, logical
The product of the method for purification acquisition crossing the present invention also has the advantage that yield is high and purity is high.
Specifically, the result from a preferred embodiment of the present invention, and the knot of the test case of the present invention
Really it can be seen that the N-toluyl Methanamide using the method for the present invention to obtain is solid state,
Convenient preservation, and, the N-toluyl Methanamide of the solid state that the method for the present invention obtains produces
The purity of product and yield are obviously higher than the purity in comparative example and yield.Further, the present invention is used
The stability of N-toluyl Methanamide product that obtains of method apparently higher than the product in comparative example
Stability.
Other features and advantages of the present invention will be described in detail in detailed description of the invention part subsequently.
Detailed description of the invention
Hereinafter the detailed description of the invention of the present invention is described in detail.It should be appreciated that this place is retouched
The detailed description of the invention stated is merely to illustrate and explains the present invention, is not limited to the present invention.
The invention provides a kind of method purifying N-toluyl crude formamide, the method includes:
Under solution condition, N-toluyl crude formamide is carried out first with acidic materials and contacts.
In the present invention, described N-toluyl crude formamide refers to, wherein contains a small amount of impurity
N-toluyl Methanamide, it is also possible to for obtained by the method for prior art without refined
N-toluyl Methanamide.In method of the present invention, particularly preferred described N-methylbenzene first
Acyl crude formamide contains the N-toluyl Methanamide of 10-97 weight %.
In the present invention, it should be strongly noted that described solution condition be those skilled in the art public affairs
Know, be and enable to described N-toluyl crude formamide and acidic materials in reaction system
In solution state, such as, can be that aqueous solution state can also be for be formed solution shape by organic solvent
State.
In the present invention, in the case of illustrating on the contrary, the scope of the term " solution " of use is also
It is not limited to the particle diameter disperse system (true solution) less than 1nm of dispersate, but refers to homogeneous liquid
State mixture, can include colloidal dispersion (colloid solution).
Acquisition in the above-mentioned method of purification of the present invention, to described N-toluyl crude formamide
There is no particular limitation for mode, and those skilled in the art can use various methods known in the art to obtain
To N-toluyl crude formamide of the present invention.
The N-methylbenzene of the solid state that the above-mentioned method of purification of the employing present invention can conveniently be preserved
Formyl Methanamide, and, it is thus achieved that the N-toluyl Methanamide good stability of solid state, have
It is beneficial to long-term preservation.The above-mentioned method of purification technique of the present invention is simple, be suitable for industrialized great production, passes through
The product that the method for purification of the present invention obtains also has the advantage that yield is high and purity is high.
Under preferable case, in the method for purification N-toluyl crude formamide of the present invention,
Described acidic materials can include organic acid and/or mineral acid；The most described acidic materials can include
At least one in HCl, sulphuric acid, phosphoric acid, trifluoroacetic acid and p-methyl benzenesulfonic acid；Particularly preferred described acid
Property material is sulphuric acid.
According to the method for purification N-toluyl crude formamide of the present invention, the most described acid
Property material is provided by acid solution, and the concentration of described acid solution is 0.1-100 weight %；The most described acid
The concentration of solution is 5-98 weight %；The concentration of particularly preferred described acid solution is 30-98 weight %.
In the method for purification N-toluyl crude formamide of the present invention, described acid
The consumption of matter for make described N-toluyl crude formamide carry out with acidic materials first contact after
The pH value of the solution obtained is 0.1-4, and the most described pH value is 1-3.5.The inventors found that
When the consumption of described acidic materials makes described N-toluyl crude formamide carry out with acidic materials
When the pH value of the solution obtained after the first contact is 0.1-4, obtain through method of purification of the present invention
The purity of the N-toluyl Methanamide obtained is high, and yield is high.In the case of Te Bieyouxuan, this
Bright inventor finds, when the consumption of described acidic materials makes described N-toluyl Methanamide thick
Product carry out with acidic materials first contact after the pH value of solution that obtains when being 1-3.5, through the present invention
The purity of the N-toluyl Methanamide that described method of purification obtains and yield reach optimum simultaneously.
According to the method for purification N-toluyl crude formamide of the present invention, described first connects
The condition touched may include that Contact Temperature is subzero 10 DEG C to 100 DEG C above freezing；Preferably Contact Temperature is
10-50℃；More preferably Contact Temperature is 20-25 DEG C.
According to the method for purification N-toluyl crude formamide of the present invention, described first connects
The condition touched may include that time of contact is 0.2-5h；Preferably time of contact is 0.5-3h；More preferably connect
The tactile time is 1-2.5h.
In the method for purification N-toluyl crude formamide of the present invention, the most described N-
Toluyl crude formamide include the compound shown in the compound shown in formula (1), formula (2),
Compound shown in formula (3) and at least one in the compound shown in formula (4) and N-methylbenzene
Formyl Methanamide:
Under preferable case, in the method for purification N-toluyl crude formamide of the present invention,
Described N-toluyl crude formamide can contain the N-methylbenzene first of 10-97 weight % especially
Acyl Methanamide, more preferably contains the N-toluyl Methanamide of 30-95 weight %, particularly preferably contains
The N-toluyl Methanamide of 50-90 weight %.
In the present invention, particularly preferred formula (1) described in described N-toluyl crude formamide
Compound, the compound shown in formula (3) and formula (4) institute shown in shown compound, formula (2)
The content total amount of the compound shown is 3-80 weight %, more preferably 10-50 weight %.
According to the method for purification N-toluyl crude formamide of the present invention, particularly preferred institute
State N-toluyl crude formamide by methyl benzoylformate is carried out with methylamine second contact and
Obtain.It was found by the inventors of the present invention that contact when methyl benzoylformate is carried out second with methylamine by employing
And the N-toluyl crude formamide obtained carry out of the present invention purify time, it is possible to substantially change
The pot-life of the kind N-toluyl Methanamide obtained, i.e. significantly improve the solid state of acquisition
The stability of N-toluyl Methanamide.
In the present invention, it should be strongly noted that when described N-toluyl crude formamide be
By methyl benzoylformate is carried out with methylamine second contact and obtain time, preferably the present invention's is described
N-toluyl crude formamide can connect containing methyl benzoylformate and methylamine are carried out second
Any one or more impurity in the reactant mixture obtained after touch.
One according to the present invention preferred embodiment, in purification N-methylbenzene first of the present invention
In the method for acyl crude formamide, the second contact of the present invention can be carried out in the presence of solvent-free.
According to another preferred embodiment of the present invention, the second contact of the present invention is having solvent to deposit
Under carry out.
Preferably, in the present invention, when described second contact is carried out in the presence of a solvent, described molten
Agent can include at least one in alcohol, ether, ester, chlorohydrocarbon and unsubstituted hydrocarbon；The most described solvent
Including methanol, ethanol, oxolane, 1,4-dioxane, toluene, dichloroethanes, ethyl acetate and
At least one in essence of Niobe；The most described solvent is methanol.
According to the method for purification N-toluyl crude formamide of the present invention, described second connects
The temperature touched can be subzero 10 DEG C to 100 DEG C above freezing；It is preferably 0-50 DEG C；More preferably 2-10 DEG C.
According to the method for purification N-toluyl crude formamide of the present invention, described second
In contact, described methyl benzoylformate can be 1:0.2-5 with the consumption mol ratio of methylamine；It is preferably
1:1-3；More preferably 1:1.5-2.
According to the method for purification N-toluyl crude formamide of the present invention, under preferable case,
The method also includes: N-toluyl crude formamide is carried out with acidic materials first contact after
To mixture carry out solid-liquid separation, and obtained solid (N-toluyl Methanamide) is entered
Row is dried.
According to method of the present invention, public affairs that the feed postition of various raw materials is those skilled in the art
Knowing, the feed postition of raw material involved in embodiments of the invention etc. is only the most concrete of the present invention
Embodiment, those skilled in the art should not be construed as the restriction to technical scheme.
In method of the present invention, in order to regulate in the pH value of solution is the framework of the present definition,
Common solvent, such as water etc. can be added in solution.Water in the method for the present invention can be deionization
Water.
The N-toluyl Methanamide obtained by the above-mentioned method of purification of the present invention is for convenience of consolidating of preserving
Body state, and the N-toluyl Methanamide good stability of solid state, be conducive to long-term preservation.
The above-mentioned method of purification technique of the present invention is simple, be suitable for industrialized great production, by the purification side of the present invention
The product that method obtains also has the advantage that yield is high and purity is high.
In the present invention, in the case of illustrating on the contrary, described contact or mixing can be in stirrings
Under conditions of carry out.The speed of stirring can be the selection of routine in this area.
The end points of scope presently disclosed and any value are not limited to this accurate scope or value, these
Scope or value should be understood to the value comprised close to these scopes or value.
Hereinafter will be described the present invention by embodiment.In following example, the most especially
In the case of explanation, the raw material used is all from being purchased.N-toluyl crude formamide Chinese style (1)
Compound shown in shown compound, formula (2) and N-toluyl Methanamide all pass through HPLC
(purchased from Agilent company, model is 6890N gas chromatograph) is detected.
In the following Examples and Comparative Examples, the yield of described N-toluyl Methanamide=[(actual
To the N-toluyl first of weight × obtain through the method for the present invention of N-toluyl Methanamide
The purity of amide)/the theoretical N-toluyl Methanamide that obtains is produced by methyl benzoylformate
Weight] × 100%.
Embodiment 1
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
250mL methanol and 85.4g methyl benzoylformate (96 is added in the four-hole bottle of 1000mL
Weight %), stirring is cooled to 0 DEG C, the methanol solution of the methylamine of 27 weight % of addition 115g, and about 3
Hour add complete, insulation reaction 24 hours, filter at 1 DEG C, and collect filtering residue and filtrate respectively,
Described filtering residue is N-toluyl crude formamide of the present invention (wherein, containing formula (1)
Compound totally 3 weight % shown in shown compound and formula (2), the N-methyl containing 95 weight %
Benzoyl Methanamide, surplus is the compound shown in formula (3) and the compound shown in formula (4)).
N-toluyl crude formamide and the described filtrate of above-mentioned acquisition are proceeded in reaction bulb,
Add water 340mL, adds the sulphuric acid 22.3g of 98 weight % at 20 DEG C, and regulation pH value is 3, stirs 1
Hour, filtering, be dried at 60 DEG C, obtain solid dry product A 74.8g altogether, purity is 99.2%, and yield is (also
I.e. weight yield, lower same) 91%.
Comparative example 1
This comparative example uses the method disclosed in CN102341378A to carry out.Specifically:
250mL methanol and 85.4g methyl benzoylformate (96 is added in the four-hole bottle of 1000mL
Weight %), stirring and controlling temperature is 17 DEG C, adds the methylamine of 32g, reacts 5 hours, at 1 DEG C
Lower filtration, and collect filtering residue and filtrate respectively, it is thick that described filtering residue is N-toluyl Methanamide
Product.By described N-toluyl crude formamide at 25 DEG C of (notes: if being dried at 60 DEG C, the most entirely
Portion obtain the product of solution state and without solid state) under be dried, obtain solid dry product D-1, yield is 30%.
Wherein, containing shown in the compound shown in formula (1) and formula (2) in described solid dry product D-1
The N-toluyl Methanamide of compound totally 5 weight % and 93 weight %, surplus is formula (3) institute
Compound shown in the compound shown and formula (4), and described filtrate is contained the formula (1) of 49 weight %
Shown compound.
Embodiment 2
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
250mL methanol and 85.4g methyl benzoylformate (96 is added in the four-hole bottle of 1000mL
Weight %), stirring is cooled to 5 DEG C, the methanol solution of the methylamine of 27 weight % of addition 115g, and about 2.5
Hour add complete, insulation reaction 24 hours, filter at 1 DEG C, and collect filtering residue and filtrate respectively,
Described filtering residue is N-toluyl crude formamide of the present invention (wherein, containing formula (1)
Compound totally 5 weight % shown in shown compound and formula (2), and possibly together with 92 weight %
N-toluyl Methanamide, surplus is the compound shown in formula (3) and the compound shown in formula (4)).
Proceed to, in reaction bulb, add by N-toluyl crude formamide and the described filtrate of above-mentioned acquisition
Enter the sulfur acid for adjusting pH value of 60 weight % to 2, stir 1 hour, filter, be dried at 60 DEG C, must consolidate
Soma product B 75.7g altogether, purity is 99%, and yield is 92%.
Embodiment 3
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
250mL methanol and 85.4g methyl benzoylformate (96 is added in the four-hole bottle of 1000mL
Weight %), stirring is cooled to 3 DEG C, the methanol solution of the methylamine of 27 weight % of addition 115g, and about 2.5
Hour add complete, insulation reaction 24 hours, filter at 1 DEG C, and collect filtering residue and filtrate respectively,
Described filtering residue is N-toluyl crude formamide of the present invention (wherein, containing formula (1)
Compound totally 3 weight % shown in shown compound and formula (2), and possibly together with 94 weight %
N-toluyl Methanamide, surplus is the compound shown in formula (3) and the compound shown in formula (4)).
N-toluyl crude formamide and the described filtrate of above-mentioned acquisition are proceeded in reaction bulb,
Add water 340mL, adds the sulfur acid for adjusting pH value of 98 weight % to 2.5, stir 1 hour at 15 DEG C,
Filtering, be dried at 60 DEG C, obtain solid dry product C 75.9g altogether, purity is 98.9%, and yield is 92.1%.
Embodiment 4
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
The present embodiment uses method same as in Example 1 to obtain N-methylbenzene same as in Example 1
Formyl crude formamide, and, by N-toluyl crude formamide and the filtrate of above-mentioned acquisition
Proceeding in reaction bulb, add water 340mL, adds the sulphuric acid of 98 weight % at 20 DEG C, and regulation pH value is 4,
Stirring 1 hour, filter, be dried at 60 DEG C, obtain solid dry product D 74.5g altogether, purity is 96.5%,
Yield 88.2%.
Embodiment 5
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
The present embodiment uses method same as in Example 2 to obtain N-methylbenzene same as in Example 2
Formyl crude formamide, and, by N-toluyl crude formamide and the filtrate of above-mentioned acquisition
Proceed in reaction bulb, add the sulfur acid for adjusting pH value of 60 weight % to 0.5, stir 1 hour, filter,
Being dried at 60 DEG C, obtain solid dry product E 73.1g altogether, purity is 95.8%, and yield is 85.9%.
Embodiment 6
The present embodiment is used for N-toluyl crude formamide of the present invention and the present invention are described
The method of purification N-toluyl crude formamide.
The present embodiment uses method same as in Example 3 to obtain N-methylbenzene same as in Example 3
Formyl crude formamide, and, by N-toluyl crude formamide and the filtrate of above-mentioned acquisition
Proceeding in reaction bulb, add water 340mL, adds the trifluoroacetic acid aqueous solution regulation of 98 weight % at 15 DEG C
PH value, to 2.5, stirs 1 hour, filters, and is dried at 60 DEG C, obtains solid dry product F 75.9g altogether, pure
Degree is 95.2%, and yield is 88.7%.
Result from embodiment 1-6 and comparative example 1 is it can be seen that use the method for the present invention to obtain
N-toluyl Methanamide be solid state, convenient preserve, and, the method for the present invention obtains
The purity of the N-toluyl Methanamide product of the solid state obtained and yield are obviously higher than comparative example
In purity and yield.
Test case
This test case is steady for the product that illustrates to prepare in above-described embodiment 1-6 and comparative example 1
Qualitative, specifically, this test case is adopted and is carried out with the following method:
The above-mentioned each product taking identical weight (1g) is respectively placed in the salable test tube of 10ml, at 25 DEG C
Lower preservation totally 90 days, and, respectively at time point as shown in table 1 from above-mentioned salable test tube
Take out sample 0.005g, and use GC to detect the content of N-toluyl Methanamide therein (i.e.
For purity) (weight %), result is shown in Table 1.
Table 1
| Product | 0 day | 10 days | 30 days | 50 days | 70 days | 90 days |
| A | 99.2 | 99.2 | 99.2 | 99.2 | 99.2 | 99.2 |
| B | 99 | 99 | 99 | 99 | 99 | 99 |
| C | 98.9 | 98.9 | 98.9 | 98.8 | 98.8 | 98.8 |
| D | 96.5 | 96.5 | 96.4 | 96.4 | 96.4 | 96.4 |
| E | 95.8 | 95.8 | 95.8 | 95.6 | 95.6 | 95.6 |
| F | 95.2 | 95.2 | 95.1 | 95.1 | 95 | 95 |
| D-1 | 93 | 90.4 | 85.5 | 85.4 | 85.4 | 85.4 |
Result from table 1 is it can be seen that use the N-toluyl first that the method for the present invention obtains
The stability of amide products is apparently higher than the stability of the product in comparative example.
The preferred embodiment of the present invention described in detail above, but, the present invention is not limited to above-mentioned reality
Execute the detail in mode, in the technology concept of the present invention, can be to the technical side of the present invention
Case carries out multiple simple variant, and these simple variant belong to protection scope of the present invention.
It is further to note that each the concrete technology described in above-mentioned detailed description of the invention is special
Levy, in the case of reconcilable, can be combined by any suitable means, in order to avoid need not
The repetition wanted, various possible compound modes are illustrated by the present invention the most separately.
Additionally, combination in any can also be carried out between the various different embodiment of the present invention, as long as its
Without prejudice to the thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (15)
1. the method purifying N-toluyl crude formamide, the method includes: deposit at solvent
Under, methyl benzoylformate is carried out second with methylamine and contacts, obtain containing N-toluyl first
The material of crude amide；Then by the described material containing N-toluyl crude formamide with acid
Material carries out the first contact；Wherein, described methyl benzoylformate is 1 with the consumption mol ratio of methylamine:
1.5-5；Described solvent is methanol；Described N-toluyl crude formamide includes shown in formula (1)
Compound, the compound shown in formula (2), shown in the compound shown in formula (3) and formula (4)
At least one in compound and N-toluyl Methanamide:
Method the most according to claim 1, wherein, described acidic materials are organic acid and/or nothing
Machine acid.
Method the most according to claim 1, wherein, described acidic materials are HCl, sulphuric acid,
At least one in phosphoric acid, trifluoroacetic acid and p-methyl benzenesulfonic acid.
Method the most according to claim 1, wherein, described acidic materials are sulphuric acid.
Method the most according to claim 1, wherein, described acidic materials are provided by acid solution,
The concentration of described acid solution is 0.1-100 weight %.
Method the most according to claim 5, wherein, the concentration of described acid solution is 5-98 weight %.
Method the most according to claim 6, wherein, the concentration of described acid solution is 30-98 weight
Amount %.
8. according to the method described in any one in claim 1-7, wherein, described acidic materials
Consumption for make described N-toluyl crude formamide carry out with acidic materials first contact after obtain
The pH value of solution be 0.1-4.
Method the most according to claim 1, wherein, the condition of described first contact includes: connect
Tactile temperature is subzero 10 DEG C to 100 DEG C above freezing, and time of contact is 0.2-5h.
Method the most according to claim 1, wherein, the condition of described first contact includes: connect
Tactile temperature is 10-50 DEG C, and time of contact is 0.5-3h.
11. methods according to claim 1, wherein, the condition of described first contact includes: connect
Tactile temperature is 20-25 DEG C, and time of contact is 1-2.5h.
12. methods according to claim 11, wherein, at described N-toluyl Methanamide
In crude product, the content of described N-toluyl Methanamide is 10-97 weight %.
13. methods according to claim 1, wherein, the temperature of described second contact is subzero 10 DEG C
To 100 DEG C above freezing.
14. methods according to claim 1, wherein, the temperature of described second contact is 0-50 DEG C.
15. methods according to claim 1, wherein, the temperature of described second contact is 2-10 DEG C.
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| CN102341378A (en) * | 2009-03-11 | 2012-02-01 | 日本曹达株式会社 | Process for preparation of 1-alkyl-5-benzoyl-1h-tetrazole derivatives |
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