CN1869006A - 2,2,2-trifluoro-N-(4-methoxy-2-methyl benzene) imine acyl chloride and its synthesis method - Google Patents
2,2,2-trifluoro-N-(4-methoxy-2-methyl benzene) imine acyl chloride and its synthesis method Download PDFInfo
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- CN1869006A CN1869006A CN 200610028163 CN200610028163A CN1869006A CN 1869006 A CN1869006 A CN 1869006A CN 200610028163 CN200610028163 CN 200610028163 CN 200610028163 A CN200610028163 A CN 200610028163A CN 1869006 A CN1869006 A CN 1869006A
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- methoxyl group
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- toluene
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A 2,2,2-trifluoro-N-(4-methoxy-2-toluene) iminoacyl chloride is prepared through adding triphenyl phosphine, triethane and CCl4 into reactor under protection of N2, stirring while cooling to O deg.C by ice water bath, adding trifluoroacetic acid, stirring, adding 4-methoxy-2-methylphenylamine, heating, reaction, vacuum distilling to remove CCl4, immersing in petroether, filter, washing the solid with petroether, centrifugal separation of solvent from liquid, and chromatography by alkaline alumina column to obtain light yellow liquid.
Description
Technical field
The present invention relates to a kind of fluorine-containing imine acyl chloride compound and synthetic method thereof, particularly 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride compound and synthetic method thereof.
Background technology
All contain heteroatoms at present a large amount of bioactive compoundss, and heterogeneous ring compound is the hugest class of number in organic compound, many materials that play an important role in physiological process.Imine acyl chloride is built soon as synthetic, because it has more active carbon chlorine key, plays important effect in synthesizing heterocyclic compounds.Methyl on the phenyl ring also is more active reflecting point, for example: can connect a large amount of useful groups by grignard reaction after the bromination.Have on the phenyl ring of a lot of medicines and contain methoxyl group, certain property of medicine effect is arranged.
In addition, in the pharmaceutical chemistry field, fluorine atom or a perfluoroalkyl are incorporated into and are considered to one of most effectual way that host compound is modified in the host molecule.Because the fluorine atom radius is little, has bigger electronegativity again, its formed C-F key bond energy is than big many of c h bond bond energy, the stability and the physiologically active of organofluorine compound have been increased significantly, fluorinated organic compound also has higher fat-soluble and hydrophobicity in addition, promote it to absorb in vivo and transmission speed, physiological action is changed.Have characteristics such as consumption is few, toxicity is low, drug effect is high, metabolic capacity is strong so a lot of fluorine-containing medicines and agricultural chemicals are relative on performance, this makes its proportion in the new pharmaceutical pesticide species more and more higher.
Summary of the invention:
One of purpose of the present invention is to provide a kind of new compound 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride.
Two of purpose of the present invention is to provide the synthetic method of this compound.
For achieving the above object, the reaction mechanism that the inventive method has adopted is:
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride is characterized in that the structure of this compound is:
2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride
The physical parameter of this compound:
Molecular formula: C
10H
9ClF
3NO
Structural formula:
Chinese named: 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride
English name: 2,2,2-trifluoro-N-(4-methoxy-2-methylphenyl) acetimidoyl chloride
Molecular weight: 251.6
Outward appearance: weak yellow liquid
Infrared spectra (adopting the Perkin-Elmer983G infrared spectrometer, liquid-film method):
υmax(cm
-1)：2959，2840，1670，1603，1496，1282，1248，1219，1197，1158，927，800，723.
Proton nmr spectra (500MHz, CDCl
3): 7.187,7.170 (d, J=8.5Hz, 1H, ArH); 6.82～6.75 (m, 2H, ArH); 3.808 (s, 3H, OCH
3); 2.230 (s, 3H, Ar-CH
3).
Nucleus magnetic resonance fluorine spectrum (470MHz, CDCl
3, interior mark: C
6F
6): δ=-71.16 (s, CF
3).
Carbon-13 nmr spectra (125MHz, CDCl
3): 159.15; 134.71; 134.24; 129.13,128.79,128.45,128.11 (J=42.5Hz); 120.68; 120.25,118.05,115.84,113.64 (J=275Hz); 115.95; 111.30; 55.32; 18.00.
A kind of 2,2, the synthetic method of 2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride, it is characterized in that this method has following steps: under the nitrogen protection, be solvent with the tetracol phenixin, in reaction vessel, add triphenylphosphine and triethylamine, under ice-water bath, stir and reduce to 0 ℃; Add trifluoroacetic acid again, stirred 10～20 minutes, add 4-methoxyl group-2-aminotoluene at last, the mol ratio of four kinds of reactant triphenylphosphines, triethylamine, trifluoroacetic acid, 4-methoxyl group-2-aminotoluene is: 2.5～3.5: 1～1.2: 1: 1～1.2; When being heated to the beginning vigorous reaction, remove thermal source immediately, reacted 3～5 hours, reaction finishes, and decompression steams the solvent in the reaction soln, adds sherwood oil then in bottle, soaks, and suction filtration is with the solid in the petroleum ether B; The liquid that obtains is spun off solvent, use the alkali alumina column chromatography for separation, eluent is that volume ratio is 40: 1 the sherwood oil and the mixed solution of ethyl acetate, gets weak yellow liquid at last, is 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride.
Raw material of the present invention is easy to get, and operates very simply, and one kettle way is synthetic.This method productive rate height is fit to scale operation.
Embodiment:
Embodiment one: add triphenyl phosphorus 3.05 grams in 50 milliliters the flask with three necks,round bottom that reflux condensing tube is housed, 10 milliliters in tetracol phenixin, 0.56 milliliter of triethylamine, 0.3 milliliter of trifluoroacetic acid, ice bath stirred 10 minutes, add 4-methoxyl group-2-aminotoluene 0.53 gram, oil bath slowly is heated to 60 ℃ of reactions and begins to cause, have solid to generate, reheat refluxes to react in 3 hours and finishes, and decompression steams the solvent in the reaction soln, in bottle, add sherwood oil then, soak, suction filtration is with the solid in the petroleum ether B; The liquid that obtains is spun off solvent, getting weak yellow liquid with alkali alumina column chromatography (eluent is that volume ratio is 40: 1 the sherwood oil and the mixed solution of ethyl acetate) is product 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride 0.87 gram (89%).
Embodiment two: add triphenyl phosphorus 30.5 grams in 250 milliliters the flask with three necks,round bottom that reflux condensing tube is housed, 150 milliliters in tetracol phenixin, 5.6 milliliters of triethylamines, 3.0 milliliters of trifluoroacetic acids, ice bath stirred 15 minutes, add 4-methoxyl group-2-aminotoluene 5.3 grams, oil bath slowly is heated to 60 ℃ of reactions and begins to cause, have solid to generate, reheat refluxes to react in 3 hours and finishes, and decompression steams the solvent in the reaction soln, in bottle, add sherwood oil then, soak, suction filtration is with the solid in the petroleum ether B; The liquid that obtains is spun off solvent, getting weak yellow liquid with alkali alumina column chromatography (eluent is that volume ratio is 40: 1 the sherwood oil and the mixed solution of ethyl acetate) is product 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride 7.9 grams (81%).
Embodiment three: add triphenyl phosphorus 305 grams in 2 liters the flask with three necks,round bottom that reflux condensing tube is housed, 1 liter in tetracol phenixin, 56 milliliters of triethylamines, 30 milliliters of trifluoroacetic acids, ice bath stirred 20 minutes, add 4-methoxyl group-2-aminotoluene 53 grams, oil bath slowly is heated to 60 ℃ of reactions and begins to cause, have solid to generate, reheat refluxes to react in 3.5 hours and finishes, and decompression steams the solvent in the reaction soln, in bottle, add sherwood oil then, soak, suction filtration is with the solid in the petroleum ether B; The liquid that obtains is spun off solvent, getting weak yellow liquid with alkali alumina column chromatography (eluent is that volume ratio is 40: 1 the sherwood oil and the mixed solution of ethyl acetate) is product 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride 75.8 grams (78%).
Claims (2)
1. one kind 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride compound is characterized in that the structure of this compound is:
2. one kind according to claim 12,2, the synthetic method of 2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride, it is characterized in that, this method has following steps: under the nitrogen protection, with the tetracol phenixin is solvent, adds triphenylphosphine and triethylamine in reaction vessel, stirs under ice-water bath and reduces to 0 ℃; Add trifluoroacetic acid again, stirred 10～20 minutes, add 4-methoxyl group-2-aminotoluene at last, the mol ratio of four kinds of reactant triphenylphosphines, triethylamine, trifluoroacetic acid, 4-methoxyl group-2-aminotoluene is: 2.5～3.5: 1～1.2: 1: 1～1.2; When being heated to the beginning vigorous reaction, remove thermal source immediately, reacted 3～5 hours, reaction finishes, and decompression steams the solvent in the reaction soln, adds sherwood oil then in bottle, soaks, and suction filtration is with the solid in the petroleum ether B; The liquid that obtains is spun off solvent, use the alkali alumina column chromatography for separation, eluent is that volume ratio is 40: 1 the sherwood oil and the mixed solution of ethyl acetate, gets weak yellow liquid at last, is 2,2,2-three fluoro-N-(4-methoxyl group-2-toluene) imine acyl chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610028163 CN1869006A (en) | 2006-06-27 | 2006-06-27 | 2,2,2-trifluoro-N-(4-methoxy-2-methyl benzene) imine acyl chloride and its synthesis method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200610028163 CN1869006A (en) | 2006-06-27 | 2006-06-27 | 2,2,2-trifluoro-N-(4-methoxy-2-methyl benzene) imine acyl chloride and its synthesis method |
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| Publication Number | Publication Date |
|---|---|
| CN1869006A true CN1869006A (en) | 2006-11-29 |
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|---|---|---|---|
| CN 200610028163 Pending CN1869006A (en) | 2006-06-27 | 2006-06-27 | 2,2,2-trifluoro-N-(4-methoxy-2-methyl benzene) imine acyl chloride and its synthesis method |
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2006
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