CN103360339A - Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol - Google Patents
Green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol Download PDFInfo
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- CN103360339A CN103360339A CN2013103502522A CN201310350252A CN103360339A CN 103360339 A CN103360339 A CN 103360339A CN 2013103502522 A CN2013103502522 A CN 2013103502522A CN 201310350252 A CN201310350252 A CN 201310350252A CN 103360339 A CN103360339 A CN 103360339A
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- aminobenzothiazole
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P20/584—Recycling of catalysts
Abstract
The invention provides a green method for catalytically synthesizing 2'-aminobenzothiazolyl-arylmethyl-2-naphthol, belonging to the field of organic chemical synthesis. The method comprises the following steps: carrying out synthetic reaction, wherein the aromatic aldehyde:2-aminobenzothiazole:beta-naphthol mol ratio is 1:1:1, the bissulfonate acidic ion liquid catalyst accounts for 5-8 mol% of the aromatic aldehyde, the reaction temperature is 80-95 DEG C, the reaction time is 3-10 minutes, and the volume (ml) of the reaction solvent water is 3-5 times of the molar weight (mmol) of the aromatic aldehyde; and after the reaction is finished, cooling to room temperature, carrying out vacuum filtration, recrystallizing the filter residue with 95% ethanol, and carrying out vacuum drying to obtain the 2'-aminobenzothiazolyl-arylmethyl-2-naphthol.Compared with other synthesis methods, the invention has the characteristics of high catalytic activity, low catalyst consumption, recyclable catalyst, low environmental pollution in the whole process, simple and convenient after-treatment and the like.
Description
Technical field
The invention belongs to the organic chemical synthesis field, be specifically related to a kind of green catalysis synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal.
Background technology
The heterogeneous ring compound that contains thiazole ring has broad-spectrum biological activity, can be used as local anesthetic, and have the effects such as anticonvulsion, antiviral, antibiotic, desinsection, anti-inflammatory and antianaphylaxis, wherein containing aminothiazole lopps compound has active than Johnson ﹠ Johnson's reason, can be used for treatment allergy, hypertension, osteoporosis, asthma, cancer, HIV virus, aspect cytobiology, also be widely used simultaneously.In addition, it or the good intermediate of a class, a series of reaction can occur in amido functional group, and the various compounds that synthesize thus have at aspects such as medicine, agricultural chemicals, dyestuffs widely to be used.Therefore, contain the concern that aminothiazole lopps derivative is subject to Pharmaceutical Chemist always, the medicine of synthetic this class formation of research and development has important theory significance and practical value.
2 '-aminobenzothiazole-arylmethyl-beta naphthal is as a kind of very important compound that contains in the aminothiazole lopps derivative, its preparation also becomes the focus that organic synthesis men are studied, and particularly synthesizes the research of the catalyst system that adopts for aromatic aldehyde, 2-aminobenzothiazole and 2-Naphthol single stage method.Such as 2007, Shaabani etc. have reported take LiCl as catalyzer, in water medium with aromatic aldehyde, 2-aminobenzothiazole and 2-Naphthol synthesized 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal, the method has advantages of Green Chemistry, but exist long reaction time, catalyst levels is large, expensive, the shortcomings such as difficult recovery (Water promoted one-pot synthesis of2 '-aminobenzothiazolomethyl naphthols and 5-(2 '-aminobenzothiazolomethyl)-hydroxyquinolines, Tetrahedron Letters, 2007,48:7291-7294).Acidic ion liquid, particularly preparation simple, to the equal stable bronsted acid ionic liquid of water and air since its have green non-pollution, to organicly have good solubility, the acidic site that is evenly distributed with mineral compound, be easy to the advantages such as product separates and can recycle and be used as green catalyst and be applied in 2 '-the synthesizing of aminobenzothiazole-arylmethyl-beta naphthal in.Such as Guo Hongyun etc. with ionic liquid [Hnmp] HSO
4(N-Methyl pyrrolidone hydrosulfate) is as catalyzer, under condition of no solvent catalysis aromatic aldehyde, 2-aminobenzothiazole and 2-Naphthol synthesized a series of 2 '-aminobenzothiazole-arylmethyl-beta naphthal, the method reaction conditions is gentle, reaction times is shorter, and productive rate is higher and environmentally friendly.In addition, catalyzer can reclaim easily, and recycles not remarkable (ionic liquid under the condition of no solvent [Hnmp] HSO of reduction of its catalytic activitys four times
4The catalysis one kettle way is synthetic 2 '-aminobenzothiazole-arylmethyl-beta naphthal, organic chemistry, 2011,51 (1): 96-100).
The acidic ion liquid that the above adopts since acidity a little less than, catalyzing and condensing aromatic aldehyde, 2-aminobenzothiazole and 2-Naphthol synthetic 2 '-process of aminobenzothiazole-arylmethyl-beta naphthal in catalytic effect still wait to improve the usage quantity of ionic liquid large (account for used aromatic aldehyde molar weight 10%) simultaneously.In addition, the number of dropouts of ionic liquid in recycling is also larger, can only recycle 4 times.All these are so that the technological process benefit of the method is lower, 2 '-be difficult to large-scale use in the suitability for industrialized production of aminobenzothiazole-arylmethyl-beta naphthal.
Summary of the invention
The object of the invention is to overcome the acidic ionic liquid catalysts usage quantity that exists in the prior art and recycle all very large shortcomings of middle number of dropouts, and provide a kind of with water as reaction solvent, make catalyzer with the disulfonic acid root acidic ion liquid that acidity is higher, product purity and productive rate all very high green catalysis synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal.
The structural formula of disulfonic acid root acidic ionic liquid catalysts used in the present invention is:
A kind of green catalysis provided by the present invention is synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal, its reaction formula is:
Aromatic aldehyde (I) in wherein reacting, 2-aminobenzothiazole (II) is 1:1:1 with the mol ratio of 2-Naphthol (III), the molar weight of disulfonic acid root acidic ionic liquid catalysts is 5～8% of used aromatic aldehyde, temperature of reaction is 80～95 ℃, reaction times is 3～10min, the volume of reaction solvent water (ml) is 3～5 times of aromatic aldehyde molar weight (mmol), reaction pressure is a normal atmosphere, be cooled to room temperature after the reaction, suction filtration, filter residue 95% ethyl alcohol recrystallization, obtain after the vacuum-drying pure 2 '-aminobenzothiazole-arylmethyl-beta naphthal (IV).The disulfonic acid root acidic ionic liquid catalysts that contains in the filtrate and the complete raw material of a small amount of unreacted, not treated reusing.
The used aromatic aldehyde (I) of the present invention is any in phenyl aldehyde, 2-chlorobenzaldehyde, 4-chlorobenzaldehyde, 4-nitrobenzaldehyde, 4-tolyl aldehyde, 4-methoxybenzaldehyde, Benzaldehyde,2-hydroxy, 2-nitrobenzaldehyde, the 2,4 dichloro benzene formaldehyde.
The preparation method of disulfonic acid root acidic ionic liquid catalysts used in the present invention sees pertinent literature (Diastereoselectivesynthesis of pyrazolines using a bifunctional Br nsted acidic ionic liquid under solvent-free conditions.Advanced Synthesis﹠amp; Catalysis, 354 (2012), 3095-3104).
The preparation method that the present invention and other acidic ion liquid are made catalyzer compares has following characteristics:
1, contain the sour density of disulfonic acid root acidic ion liquid high, catalytic activity is good, and the catalysis productive rate is high;
2, the catalyzer usage quantity is few and to recycle middle loss amount also less;
3, make water as reaction solvent, environmental pollution is little;
4, last handling process is easy, and catalyzer can just can be recycled without any processing.
Embodiment
In order more clearly to describe the present invention, now enumerate following examples, but the present invention is not limited to following embodiment, under the scope of described aim, any change all should be included within protection scope of the present invention before and after not breaking away from.The embodiment reaction product characterizes with nuclear magnetic resonance analyser and infrared spectrometer test, wherein
1That H NMR uses is Bruker AVANCE-II500MHz, and what IR adopted is the NEXUS670 Fourier infrared spectrograph.
Embodiment 1
1mmol phenyl aldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 3ml water and 0.05mmol disulfonic acid root acidic ion liquid are joined respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.80 ℃ of lower vigorous stirring reaction 5min, TLC (thin plate chromatography) detects, and raw material point disappears, be cooled to room temperature, suction filtration, gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-phenyl methyl-beta naphthal, productive rate is 94%.Directly adding phenyl aldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-phenyl methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=6.97～7.86 (m, 16H, ArH/CH), 8.80 (s, 1H ,-NH-), 10.13 (s, 1H ,-OH); IR (KBr): ν=3379,1623,1595,1544,1518,1445,1332,1270,814,750cm
-1
Embodiment 2
1mmol2-chlorobenzaldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 5ml water and 0.05mmol disulfonic acid root acidic ion liquid are joined respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.80 ℃ of lower vigorous stirring reaction 4min, TLC (thin plate chromatography) detects, and raw material point disappears, be cooled to room temperature, suction filtration, gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-(2-chloro-phenyl-) methyl-beta naphthal, productive rate is 95%.Directly adding 2-chlorobenzaldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-(2-chloro-phenyl-) methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=6.96～8.04 (m, 15H, ArH/CH), 8.82 (s, 1H ,-NH-), 9.91 (s, 1H ,-OH); IR (KBr): ν=3384,1628,1597,1543,1440,1319,1271,815,754cm
-1
Embodiment 3
1mmol4-nitrobenzaldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 5ml water and 0.05mmol disulfonic acid root acidic ion liquid are joined respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.85 ℃ of lower vigorous stirring reaction 3.5min, TLC (thin plate chromatography) detects, raw material point disappears, be cooled to room temperature, suction filtration, the gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-(4-nitrophenyl) methyl-beta naphthal, productive rate is 96%.Directly adding 4-nitrobenzaldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-(4-nitrophenyl) methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=7.06～8.14 (m, 15H, ArH/CH), 8.92 (s, 1H ,-NH-), 10.21 (s, 1H ,-OH); IR (KBr): ν=3393,1626,1599,1534,1443,1349,1270,813,753cm
-1
Embodiment 4
1mmol4-tolyl aldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 4ml water and 0.05mmol disulfonic acid root acidic ion liquid are joined respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.80 ℃ of lower vigorous stirring reaction 3min, TLC (thin plate chromatography) detects, raw material point disappears, be cooled to room temperature, suction filtration, the gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-(4-aminomethyl phenyl) methyl-beta naphthal, productive rate is 96%.Directly adding 4-tolyl aldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-(4-aminomethyl phenyl) methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=2.22 (s, 3H ,-CH
3), 6.98～7.84 (m, 15H, ArH/CH), 8.76 (s, 1H ,-NH-), 10.11 (s, 1H ,-OH); IR (KBr): ν=3373,1629,1595,1541,1453,1336,1273,1204,815,750cm
-1
Embodiment 5
1mmol4-methoxybenzaldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 4ml water and 0.08mmol disulfonic acid root acidic ion liquid are joined respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.90 ℃ of lower vigorous stirring reaction 5min, TLC (thin plate chromatography) detects, raw material point disappears, be cooled to room temperature, suction filtration, the gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-(4-p-methoxy-phenyl) methyl-beta naphthal, productive rate is 95%.Directly adding 4-methoxybenzaldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-(4-p-methoxy-phenyl) methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=3.67 (s, 3H ,-OCH
3), 6.85～7.92 (m, 15H, ArH/CH), 8.78 (s, 1H ,-NH-), 10.13 (s, 1H ,-OH); IR (KBr): ν=3374,1626,1598,1542,1510,1451,1256,1173,818,752cm
-1
Embodiment 6
With 1mmol2,4-dichlorobenzaldehyde, 1mmol2-aminobenzothiazole, 1mmol 2-Naphthol, 5ml water and 0.08mmol disulfonic acid root acidic ion liquid join respectively in the single port bottle of 25ml with stirrer and reflux condensing tube.90 ℃ of lower vigorous stirring reaction 10min, TLC (thin plate chromatography) detects, raw material point disappears, be cooled to room temperature, suction filtration, the gained filter residue obtain after with 95% aqueous ethanolic solution recrystallization, vacuum-drying straight product 2 '-aminobenzothiazole-(2,4 dichloro benzene base) methyl-beta naphthal, productive rate is 94%.Directly adding 2,4 dichloro benzene formaldehyde, 2-aminobenzothiazole and 2-Naphthol in the filtrate reuses.
2 '-aminobenzothiazole-(2,4 dichloro benzene base) methyl-beta naphthal:
1H NMR (500MHz, DMSO-d
6): δ=6.98～8.04 (m, 14H, ArH/CH), 8.88 (s, 1H ,-NH-), 9.93 (s, 1H ,-OH); IR (KBr): ν=3379,1627,1596,1540,1470,1454,1268,816,751,687cm
-1
Embodiment 7
Take embodiment 1 as probe reaction, make the active replica test of catalysts disulfonic acid root acidic ion liquid, ionic liquid is reused 5 times.The productive rate data of reaction see Table 1.
The catalyst activity replica test result that table 1 the present invention uses
| Disulfonic acid root acidic ion liquid access times | Productive rate (%) |
| 1 | 94 |
| 2 | 92 |
| 3 | 91 |
| 4 | 91 |
| 5 | 90 |
| 6 | 88 |
Can draw such conclusion by table 1 data: catalyzer in recycling process 2 '-productive rate of aminobenzothiazole-phenyl methyl-beta naphthal slightly has reduction, but the reduction amplitude is less, prove its can preparation 2 '-recycle in aminobenzothiazole-arylmethyl-beta naphthal.
Claims (3)
- A green catalysis synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal, wherein synthetic 2 '-reaction of aminobenzothiazole-arylmethyl-beta naphthal in aromatic aldehyde, the mol ratio of 2-aminobenzothiazole and 2-Naphthol is 1:1:1, the molar weight of disulfonic acid root acidic ionic liquid catalysts is 5～8% of used aromatic aldehyde, temperature of reaction is 80～95 ℃, reaction times is 3～10min, the volume of reaction solvent water (ml) is 3～5 times of aromatic aldehyde molar weight (mmol), reaction pressure is a normal atmosphere, be cooled to room temperature after the reaction, suction filtration, filter residue 95% ethyl alcohol recrystallization, obtain after the vacuum-drying pure 2 '-aminobenzothiazole-arylmethyl-beta naphthal;The structural formula of described disulfonic acid root acidic ionic liquid catalysts is:
- A kind of green catalysis as claimed in claim 1 synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal, it is characterized in that, described aromatic aldehyde is any in phenyl aldehyde, 2-chlorobenzaldehyde, 4-chlorobenzaldehyde, 4-nitrobenzaldehyde, 4-tolyl aldehyde, 4-methoxybenzaldehyde, Benzaldehyde,2-hydroxy, 2-nitrobenzaldehyde and the 2,4 dichloro benzene formaldehyde.
- A kind of green catalysis as claimed in claim 1 synthetic 2 '-method of aminobenzothiazole-arylmethyl-beta naphthal, it is characterized in that, the disulfonic acid root acidic ionic liquid catalysts that contains in the described suction filtration rear filtrate is treated reusing not.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106967095A (en) * | 2017-05-18 | 2017-07-21 | 马鞍山市泰博化工科技有限公司 | A kind of method that catalysis prepares benzothiazole quinazoline derivant |
| CN113816973A (en) * | 2021-10-27 | 2021-12-21 | 南京欣久医药科技有限公司 | Preparation method of medical intermediate benzothiazole [2, 3-b ] quinazolinedione derivative |
| CN114349718A (en) * | 2022-02-25 | 2022-04-15 | 南京苏亦欣医药科技有限公司 | Preparation method of thiadiazole derivative drug intermediate containing amino alkyl naphthol structure |
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| US2868774A (en) * | 1957-04-15 | 1959-01-13 | Eastman Kodak Co | Metallizable azo dyes prepared from amino-benzothiazole derivatives and beta-naphthol derivatives |
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Patent Citations (2)
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| US2868774A (en) * | 1957-04-15 | 1959-01-13 | Eastman Kodak Co | Metallizable azo dyes prepared from amino-benzothiazole derivatives and beta-naphthol derivatives |
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| Title |
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| AHMAD SHAABANI，等: "Water promoted one-pot synthesis of 2’-aminobenzothiazolomethyl naphthols and 5-(2’-aminobenzothiazolomethyl)-6-hydroxyquinolines", 《TETRAHEDRON LETTERS》, vol. 48, no. 41, 31 December 2007 (2007-12-31) * |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106967095A (en) * | 2017-05-18 | 2017-07-21 | 马鞍山市泰博化工科技有限公司 | A kind of method that catalysis prepares benzothiazole quinazoline derivant |
| CN106967095B (en) * | 2017-05-18 | 2019-02-26 | 马鞍山市泰博化工科技有限公司 | A kind of method that catalysis prepares benzothiazole quinazoline derivant |
| CN113816973A (en) * | 2021-10-27 | 2021-12-21 | 南京欣久医药科技有限公司 | Preparation method of medical intermediate benzothiazole [2, 3-b ] quinazolinedione derivative |
| CN113816973B (en) * | 2021-10-27 | 2022-07-12 | 江西力田维康科技有限公司 | Preparation method of medical intermediate benzothiazole [2, 3-b ] quinazolinedione derivative |
| CN114349718A (en) * | 2022-02-25 | 2022-04-15 | 南京苏亦欣医药科技有限公司 | Preparation method of thiadiazole derivative drug intermediate containing amino alkyl naphthol structure |
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