CN100357269C - 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride and its synthesis method - Google Patents
2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride and its synthesis method Download PDFInfo
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- CN100357269C CN100357269C CNB2006100281585A CN200610028158A CN100357269C CN 100357269 C CN100357269 C CN 100357269C CN B2006100281585 A CNB2006100281585 A CN B2006100281585A CN 200610028158 A CN200610028158 A CN 200610028158A CN 100357269 C CN100357269 C CN 100357269C
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- difluoro
- acyl chloride
- imine acyl
- bromo
- methyl phenyl
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Abstract
The present invention relates to a 2, 2-difluoro-N-o-bromine methyl radical phenyl imine acyl chloride compound and the synthetic method. The structural formula of the compound can be seen from a right picture. The synthesis method of the compound has the procedures that carbon tetrachloride is used as a solvent, N-bromosuccinimide and benzoyl peroxide of catalytic agents are filled, and heating and reflux are carried out for six hours to eight hours. The molar ratio of 2, 2-difluoro-N-o-tolyl imine acyl chloride and N-bromo-succinimide is 1: 1 to 1.2. Filtration is carried out under heat, tetrachloromethane is used for washing for two times, the solvent is turned off by filter liquor, column chromatography is neutral alumina, eluting agents are petroleum ether, and white solids and the preparation method for 2, 2-difluoro-N-o-bromine methyl radical phenyl imine acyl chloride can be obtained. The present invention has the advantages of simple operation and mild condition.
Description
Technical field
The present invention relates to a kind of fluorine-containing imine acyl chloride and synthetic method thereof, particularly 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride and synthetic method thereof.
Background technology
All contain O at present a large amount of bioactive compoundss, heteroatomss such as N, and heterogeneous ring compound is the hugest class of number in organic compound, many materials that in physiological process, play an important role, base as nucleic acid, amino acid all includes heterocycle structure in VITAMIN and the alkaloid.People design as required some have the functional heterogeneous ring compound of special function and purposes, useful as drug, dyestuff, biosimulation material, organic conductor, engineering macromolecular material etc.
Imine acyl chloride is built soon as synthetic, because it has more active carbon chlorine key, plays important effect in synthesizing heterocyclic compounds.Brooethyl on the phenyl ring also is more active reflecting point, can connect a large amount of useful groups by grignard reaction.
On the other hand, 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-difluoro-N-O-bromo methyl phenyl 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, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride is characterized in that, the structure of this compound is:
2, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride
The physical parameter of this compound:
Molecular formula: C
9H
7BrClF
2N
Structural formula:
Chinese named: 2, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride
English name: N-(2-(bromomethyl) phenyl)-2,2-difluoroacetimidoyl chloride
Molecular weight: 282.5
Outward appearance: white solid
Infrared spectra (adopting the Perkin-Elmer983G infrared spectrometer, liquid-film method):
υ?max(cm
-1)：2925，1691，1599，1580，1488，1453，1350，1220，1170，1070，1009，779，765，690，608.
Proton nmr spectra (500MHz, CDCl
3): 7.441～6.953 (m, 4H.ArH); 6.417,6.308,6.199 (J=54.5Hz, 1H, CF
2H); 4.404 (s, 2H, CH
2Br).
Nucleus magnetic resonance fluorine spectrum (470MHz, CDCl
3, interior mark: C
6F
6): δ=-119.0 (d, J=54.52 Hz, CF
2H).
Carbon-13 nmr spectra (125MHz, CDCl
3): 143.35; 140.69,140.43,140.17 (J=32.75Hz); 130.41; 130.20; 129.40; 127.15; 119.62; 112.11,110.15,108.18 (J=245.9Hz); 29.04.
Above-mentioned 2, the preparation method of 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride is characterized in that, this method has following steps: be solvent with the tetracol phenixin, add the benzoyl peroxide of N-bromo-succinimide and catalytic amount, reflux 6～8 hours; 2, the mol ratio of 2-difluoro-N-O-tolyl imineacyl chloride, N-bromo-succinimide: 1: 1～1.2; Filtered while hot, with the tetracol phenixin washing, filtrate spins off solvent, column chromatography for separation, eluent is a sherwood oil, getting white solid is 2, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride
The present invention's operation is very simple, mild condition.
Embodiment:
The flask with three necks,round bottom that reflux condensing tube is housed that embodiment is one: 50 milliliter, add 1.58 grams 2,2-difluoro-N-O-tolyl imineacyl chloride, 1.52 gram N-bromo-succinimides, 10 milliliters of tetracol phenixin, 0.1 gram benzoyl peroxide, reflux 6 hours, white solid appears in the solution upper strata.Filter solid while hot, wash solid at twice with 20 milliliters of tetracol phenixin, filtrate spins off solvent, and column chromatography (neutral alumina), eluent are sherwood oil, gets 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride 1.72 grams (78%).
The flask with three necks,round bottom that reflux condensing tube is housed that embodiment is two: 0.5 liters, add 15.8 grams 2,2-difluoro-N-O-tolyl imineacyl chloride, 15.2 gram N-bromo-succinimides, 60 milliliters of tetracol phenixin, 1 gram benzoyl peroxide, reflux 7 hours, white solid appears in the solution upper strata.Filter solid while hot, wash solid at twice with 100 milliliters of tetracol phenixin, filtrate spins off solvent, and column chromatography (neutral alumina), eluent are sherwood oil, gets 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride 16.3 grams (74%).
The flask with three necks,round bottom that reflux condensing tube is housed that embodiment is three: 1.5 liters, add 0.158 kilogram 2,2-difluoro-N-O-tolyl imineacyl chloride, 0.152 kilogram of N-bromo-succinimide, 0.5 liter of tetracol phenixin, 8 gram benzoyl peroxides, reflux 8 hours, white solid appears in the solution upper strata.Filter solid while hot, wash solid at twice with 500 milliliters of tetracol phenixin, filtrate spins off solvent, and column chromatography (neutral alumina), eluent are sherwood oil, gets 2,0.15 kilogram of 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride (68%).
Claims (2)
1. one kind 2, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride is characterized in that, the structure of this compound is:
2. one kind according to claim 12, the synthetic method of 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride is characterized in that, this method has following steps: be solvent with the tetracol phenixin, the benzoyl peroxide that adds N-bromo-succinimide and catalytic amount, reflux 6～8 hours; 2, the mol ratio of 2-difluoro-N-O-tolyl imineacyl chloride, N-bromo-succinimide: 1: 1～1.2; Filtered while hot, with the tetracol phenixin washing, filtrate spins off solvent, column chromatography for separation, eluent is a sherwood oil, getting white solid is 2, the 2-difluoro-N-O-bromo methyl phenyl imine acyl chloride.
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| CNB2006100281585A CN100357269C (en) | 2006-06-27 | 2006-06-27 | 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride and its synthesis method |
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| CNB2006100281585A CN100357269C (en) | 2006-06-27 | 2006-06-27 | 2,2-difluoro-N-O-bromo methyl phenyl imine acyl chloride and its synthesis method |
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| CN1869010A CN1869010A (en) | 2006-11-29 |
| CN100357269C true CN100357269C (en) | 2007-12-26 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481292B (en) * | 2009-02-25 | 2011-08-03 | 濮阳惠成化工有限公司 | Preparation of 2-bromofluorenone |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1660806A (en) * | 2004-12-15 | 2005-08-31 | 上海大学 | Method for synthesizing trifluoromethyl indole |
| CN1230419C (en) * | 2004-01-18 | 2005-12-07 | 中国科学院上海有机化学研究所 | Process for preparation of N-aryl-bromodifluoro ethyleneimino-acyl chloride |
-
2006
- 2006-06-27 CN CNB2006100281585A patent/CN100357269C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1230419C (en) * | 2004-01-18 | 2005-12-07 | 中国科学院上海有机化学研究所 | Process for preparation of N-aryl-bromodifluoro ethyleneimino-acyl chloride |
| CN1660806A (en) * | 2004-12-15 | 2005-08-31 | 上海大学 | Method for synthesizing trifluoromethyl indole |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481292B (en) * | 2009-02-25 | 2011-08-03 | 濮阳惠成化工有限公司 | Preparation of 2-bromofluorenone |
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| CN1869010A (en) | 2006-11-29 |
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Effective date of registration: 20130909 Address after: 226600 fine chemical industry park, Haian Development Zone, Haian County, Nantong, Jiangsu Patentee after: Jiangsu Tiancheng Biochemical Products Co., Ltd. Address before: 200444 Baoshan District Road, Shanghai, No. 99 Patentee before: Shanghai University |
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