CN110041223A - Using hydrazine class compound as the method for raw material oxidative synthesis azo compound - Google Patents
Using hydrazine class compound as the method for raw material oxidative synthesis azo compound Download PDFInfo
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- CN110041223A CN110041223A CN201910474831.5A CN201910474831A CN110041223A CN 110041223 A CN110041223 A CN 110041223A CN 201910474831 A CN201910474831 A CN 201910474831A CN 110041223 A CN110041223 A CN 110041223A
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- compound
- raw material
- hydrazine class
- class compound
- azo compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/20—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group the two nitrogen atoms of the functional groups being doubly-bound to each other, e.g. azoformamide
Abstract
The present invention provides a kind of methods for synthesizing azo compound, are using hydrazine class compound as raw material, and sym-closene is oxidant, and in organic solvent, in air atmosphere, under room temperature, one pot of high yield efficient has synthesized azo compound.The present invention is cheap using cheap, green non-poisonous, efficient oxidation sym-closene as oxidant, environmentally protective, and performance is stablized, safe to use；Reaction dissolvent does not need specially treated, and no coupling product generates, and post-reaction treatment is simple, and environmental pollution is small, environmentally protective, is suitable for industrialized production.
Description
Technical field
The present invention relates to the synthetic methods of azo compound, more particularly to even by raw material oxidative synthesis of hydrazine class compound
The method of nitrogen compound, belongs to technical field of organic synthesis.
Background technique
In recent years, azo-compound is widely used in as a kind of important organic matter due to its unique structure feature
Dyestuff, light-guide material etc., and have in terms of organic synthesis and be widely applied.The structural formula of azo compound is as shown below:
Wherein, R1For hydrogen, halogen, nitro；R2For 4- fluorophenyl, 4- bromophenyl, bis- trifluoromethyl of 3,5-, carboxyethyl,N,NDiethylformamide base.
In consideration of it, a large amount of synthetic strategy has been used to the preparation and synthesis of this kind of molecule of the skeleton.As diazonium coupling is anti-
It answers；Mir's Si reaction；The reductive coupling reaction of nitro compound and the oxidation reaction of hydrazine class compound, are all to prepare azo
Close the extremely effective method of object.Wherein, the oxidation reaction of hydrazine class compound shows the simple advantage of reaction method.Therefore,
Using suitable oxidant, by oxidation reaction, hydrazine class compound is converted to corresponding azo-compound, has and greatly closes
At meaning.But in the such method for oxidation registered, common oxidant is mostly that metal onidiges or other prices are more high
Expensive oxidant.
Summary of the invention
The object of the present invention is to provide a kind of simple processes, easy to operate, low in cost, environmentally protective azo chemical combination
The synthetic method of object.
The method that the present invention synthesizes azo compound, is the sym-closene (TCCA) using hydrazine class compound as raw material
In air atmosphere, azo compound is synthesized under room temperature in organic solvent for oxidant.Its reaction equation is as follows.
Wherein, R1For hydrogen, halogen, nitro；R2For 4- fluorophenyl, 4- bromophenyl, bis- trifluoromethyl of 3,5-, carboxyl second
Ester,N,NDiethylformamide base.
The molar ratio of hydrazine class compound and sym-closene (TCCA) are 1:2；Reaction time is 13 ~ 15 minutes.
Organic solvent be tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE),N,NDimethylformamide, acetonitrile, ethyl alcohol, methanol
In any one, preferred tetrahydrofuran.
The product of above-mentioned synthesis is detected through nucleus magnetic hydrogen spectrum, is shown to be the azo compound that purity is up to 97%, and azo
The yield for closing object is up to 97%.
The method of the present invention has the advantage that compared with the existing technology
1, the present invention using hydrazine class compound as raw material, using cheap, green non-poisonous, efficient oxidation sym-closene as
Azo compound is prepared in oxidant at room temperature.The operating process is related to that oxidant is cheap and easy to get, and performance is steady
It is fixed, it is safe to use and environmentally protective；
2, the present invention uses one pot process azo-compound, realizes and in high yield, efficiently synthesizes；
3, reaction carries out in air atmosphere, and reaction dissolvent does not need specially treated, and post-reaction treatment is simple, and environmental pollution is small,
It is environmentally protective, it is suitable for industrialized production.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum of 1 synthetic product azobenzene of the embodiment of the present invention, carbon spectrum.
Fig. 2 is the nucleus magnetic hydrogen spectrum of 2 synthetic product 4,4 '-difluoro azobenzene of the embodiment of the present invention, carbon spectrum.
Fig. 3 is the nucleus magnetic hydrogen spectrum of 3 synthetic product 1- of the embodiment of the present invention (4- bromophenyl) azobenzene, carbon spectrum.
Fig. 4 is the nucleus magnetic hydrogen spectrum, carbon of 4 synthetic product 1- of the embodiment of the present invention (bis- trifluoromethyl of 3,5-) azobenzene
Spectrum.
Fig. 5 is the nucleus magnetic hydrogen spectrum, carbon of 5 synthetic product 2- of the embodiment of the present invention (4- nitrobenzophenone) azo -1- carboxylic acid, ethyl ester
Spectrum.
Fig. 6 is 6 synthetic product of the embodiment of the present inventionN,NThe core of diethyl -2- (4- nitrobenzophenone) azo -1- formamide
Magnetic hydrogen spectrum, carbon spectrum.
Specific embodiment
It is described further below by process of the specific embodiment to invention synthesis azo compound.
Embodiment 1: the synthesis of azobenzene
1,2- diphenyl hydrazine (0.3 mmol) is added in 1.5 mL THF, and sym-closene (0.6 mmol) is added,
It is stirred to react 15 min at room temperature.After reaction plus water quenching are gone out, then (10 mL × 3) are extracted with ethyl acetate.Merge organic extractant phase
Liquid, and it is dry with anhydrous sodium sulfate；Organic phase after drying, which is removed by filtration desiccant and is concentrated, can obtain crude product；It is thick to produce
Object carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=10:1), and it is (orange-yellow that target product can be obtained
Solid) --- azobenzene, yield 97%, Mp67 ~ 68oC.It is as follows that it synthesizes formula:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:7.94~7.91 (m, 4H), 7.54~7.45
(m, 6H);13C NMR (100 MHz, CDCl3) δ: 152.6, 131.0, 129.1, 122.8。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 1.
The synthesis of embodiment 2:4,4 '-difluoro azobenzene
By (4,4 '-difluoro) -1,2- diphenyl hydrazine (0.3 mmol) is added in 1.5 mL THF, and sym-closene is added
(0.6 mmol), is stirred at room temperature 13 min.Reaction plus water quenching are gone out, then (10 mL x 3) is extracted with ethyl acetate.It is associated with
Machine phase extract liquor, and it is dry with anhydrous sodium sulfate.Organic phase after drying, desiccant, which is removed by filtration, and is concentrated can obtain slightly
Product.Crude product carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=10:1), and target product can be obtained
(orange/yellow solid) --- the synthesis of 4,4 '-difluoro azobenzenes, yield 91%, Mp 100 ~ 101oC.It is as follows that it synthesizes formula:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:7.93~7.89 (m, 4H), 7.18 (t,J= 8.0 Hz, 4H)；13C NMR (100 MHz, CDCl3) δ:164.3 (d, J = 250 Hz), 148.9 (d, J
= 2.0 Hz), 124.8 (d, J = 9.0 Hz), 116.0 (d, J = 23 Hz)。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 2.
The synthesis of embodiment 3:1- (4- bromophenyl) azobenzene
1- (4- bromophenyl) -1,2- diphenyl hydrazine (0.3 mmol) is added in 1.5 mL THF, and sym-closene is added
(0.6 mmol), is stirred at room temperature 14 min.Reaction plus water quenching are gone out, then (10 mL x 3) is extracted with ethyl acetate.It is associated with
Machine phase extract liquor, and it is dry with anhydrous sodium sulfate.Organic phase after drying, desiccant, which is removed by filtration, and is concentrated can obtain slightly
Product.Crude product carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=3:1), and target product can be obtained
The synthesis of (orange/yellow solid) --- 1- (4- bromophenyl) azobenzene, yield 92%, Mp 87 ~ 88oC.It is as follows that it synthesizes formula:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:7.93~7.90 (m, 2H), 7.82~7.79
(m, 2H), 7.67~7.63(m, 2H), 7.55~7.47(m, 3H)；13C NMR (100 MHz, CDCl3) δ:152.4,
151.3, 132.3, 131.3, 129.1, 125.3, 124.3, 122.9。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 3.
The synthesis of embodiment 4:1- (bis- trifluoromethyl of 3,5-) azobenzene
1- (3,5- bis- trifluoromethyl) -1,2- diphenyl hydrazine (0.3 mmol) is added in 1.5 mL THF, and is added three
Symclosene (0.6 mmol), is stirred at room temperature 14 min.Reaction plus water quenching are gone out, then (10 mL x are extracted with ethyl acetate
3).Merge organic phase extract liquor, and dry with anhydrous sodium sulfate.Organic phase after drying is removed by filtration desiccant and is concentrated
It can obtain crude product.Crude product carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=10:1)
Obtain target product (orange/yellow solid) --- 1- (3,5- bis- trifluoromethyl) azobenzene, yield 93%, Mp 70 ~
71oC.It is as follows that it synthesizes formula:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:8.36 (s, 2H); 7.99~7.96 (m,
3H), 7.57~7.55 (m, 3H)；13C NMR (100 MHz, CDCl3) δ:152.8, 152.0, 132.7 (q, J =
34 Hz), 132.5, 129.3, 123.8 (q, J = 4 Hz), 123.4, 123.1 (q, J = 271 Hz),
123.0(d, J = 3 Hz)。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 4.
The synthesis of embodiment 5:2- (4- nitrobenzophenone) azo -1- carboxylic acid, ethyl ester
2- (4- nitrobenzophenone) diazanyl -1- carboxylic acid, ethyl ester (0.3 mmol) is added in 1.5 mL THF, and TCCA(0.6 is added
Mmol), 15 min are stirred at room temperature.Reaction plus water quenching are gone out, then (10 mL x 3) is extracted with ethyl acetate.Merge organic phase
Extract liquor, and it is dry with anhydrous sodium sulfate.Organic phase after drying, desiccant, which is removed by filtration, and is concentrated slightly to be produced
Object.Crude product carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=2:1), and target product can be obtained
(Orange red solid) --- 2- (4- nitrobenzophenone) azo -1- carboxylic acid, ethyl ester, yield 94%, Mp 58 ~ 59oC.It synthesizes formula such as
Under:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:8.42~8.39 (m, 2H), 8.08~8.04
(m, 2H), 4.56 (q, J = 7.2 Hz, 2H), 1.49 (t, J= 7.2 Hz, 3H)；13C NMR (100 MHz,
CDCl3) δ:161.5, 154.2, 150.3, 124.8, 124.2, 65.0, 14.1。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 5.
Embodiment 6:N,NThe synthesis of diethyl -2- (4- nitrobenzophenone) azo -1- formamide
It willN,NDiethyl -2- (4- nitrobenzophenone) diazanyl -1- formamide (0.3 mmol) is added in 1.5 mL THF, and is added
TCCA(0.6 mmol), 13 min are stirred at room temperature.Reaction plus water quenching are gone out, then (10 mL x 3) is extracted with ethyl acetate.It closes
And organic extractant phase liquid, and it is dry with anhydrous sodium sulfate.Organic phase after drying, desiccant, which is removed by filtration, and is concentrated to obtain
To crude product.Crude product carries out chromatography post separation (eluant, eluent is petroleum ether: ethyl acetate=1:1), and target can be obtained
Product (orange solids) ---N,NDiethyl -2- (4- nitrobenzophenone) azo -1- formamide, yield 91%, Mp101 ~
103oC.It is as follows that it synthesizes formula:
The nuclear magnetic data of product is as follows:1H NMR (400 MHz, CDCl3) δ:8.40 (d, J = 8.8 Hz, 2H),
8.04 (d, J = 8.8 Hz, 2H), 3.61 (q, J = 6.8 Hz, 2H), 3.52 (q, J = 7.2 Hz, 2H),
1.34 (t, J = 6.8 Hz, 3H), 1.20 (t, J= 7.2 Hz, 3H)；13C NMR (100 MHz, CDCl3) δ:
161.2, 154.7, 149.8, 124.8, 123.9, 41.9, 41.7, 14.4, 12.8。
The nucleus magnetic hydrogen spectrum of product, carbon spectrum are shown in Fig. 6.
Claims (5)
1. being the trichlorine using hydrazine class compound as raw material using hydrazine class compound as the method for raw material oxidative synthesis azo compound
Isocyanuric acid is oxidant, in organic solvent, in air atmosphere, is reacted under room temperature；It is extracted after reaction, is dense
Contracting, column chromatography for separation are to get azo compound.
2. as described in claim 1 using hydrazine class compound as the method for raw material oxidative synthesis azo compound, it is characterised in that:
The structural formula of hydrazine class compound is as follows:
Wherein, R1For hydrogen, halogen, nitro；R2For 4- fluorophenyl, 4- bromophenyl, bis- trifluoromethyl of 3,5-, carboxyethyl,N,NDiethylformamide base.
3. as described in claim 1 using hydrazine class compound as the method for raw material oxidative synthesis azo compound, it is characterised in that:
The molar ratio of hydrazine class compound and sym-closene is 1:2.
4. as described in claim 1 using hydrazine class compound as the method for raw material oxidative synthesis azo compound, it is characterised in that:
The reaction time is 13 ~ 15 minutes under room temperature.
5. as described in claim 1 using hydrazine class compound as the method for raw material oxidative synthesis azo compound, it is characterised in that:
Organic solvent be tetrahydrofuran, ether, methyl tertiary butyl ether(MTBE),N,NIt is dimethylformamide, acetonitrile, ethyl alcohol, any in methanol
It is a kind of.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110551042A (en) * | 2019-09-03 | 2019-12-10 | 云南民族大学 | preparation method of aromatic azo organic compound |
| CN113754558A (en) * | 2021-08-05 | 2021-12-07 | 桂林理工大学 | Method for synthesizing azobenzene by catalyzing C-N coupling reaction through copper salt |
| CN115417790A (en) * | 2022-10-09 | 2022-12-02 | 山东大学 | Novel azo foaming agent and synthesis method thereof |
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| CN113754558A (en) * | 2021-08-05 | 2021-12-07 | 桂林理工大学 | Method for synthesizing azobenzene by catalyzing C-N coupling reaction through copper salt |
| CN113754558B (en) * | 2021-08-05 | 2023-06-23 | 桂林理工大学 | Method for synthesizing azobenzene through copper salt catalyzed C-N coupling reaction |
| CN115417790A (en) * | 2022-10-09 | 2022-12-02 | 山东大学 | Novel azo foaming agent and synthesis method thereof |
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