CN1718574A - 1,2,3, the chemical synthesis process of 4-tetrazole compound - Google Patents
1,2,3, the chemical synthesis process of 4-tetrazole compound Download PDFInfo
- Publication number
- CN1718574A CN1718574A CN 200410052775 CN200410052775A CN1718574A CN 1718574 A CN1718574 A CN 1718574A CN 200410052775 CN200410052775 CN 200410052775 CN 200410052775 A CN200410052775 A CN 200410052775A CN 1718574 A CN1718574 A CN 1718574A
- Authority
- CN
- China
- Prior art keywords
- nitrile
- chemical synthesis
- synthesis process
- sodiumazide
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
A kind of 1,2,3, the chemical synthesis process of 4-tetrazole compound comprises following sequential steps: (1) provides trifluoromethanesulfonic acid zinc water-soluble solution A, with nitrile and sodiumazide in above-mentioned solution A, under 50～100 ℃, react reaction solution; (2) step (1) gained reaction solution is added the acid neutralization, filter to such an extent that filter cake is a product, filtrate is solution B.Chemical synthesis process beneficial effect of the present invention is embodied in: reaction yield height (generally more than 80%), production cost are low; Operational path advanced person, reaction conditions gentleness; Catalyst levels is few and recyclablely apply mechanically, do not have substantially the three wastes; Water can be avoided using of organic solvent to greatest extent as solvent and pollute.
Description
(1) technical field
The present invention relates to a kind of 1,2,3, the chemical synthesis process of 4-tetrazole compound.
(2) background technology
1,2,3, the 4-tetrazole compound is widely used in the synthetic of agricultural chemicals, medicine and dyestuff, has very high practical value.
In the prior art, 1,2,3, the chemosynthesis of 4-tetrazole compound is to prepare in organic solvent with amine or amine salt catalyzer.As US 4,097,479 reacting under the katalysis of 1mol amine salt with 1mol nitrile and 1mol sodiumazide of proposition make.This method needs equimolar amine salt as catalyzer, and temperature of reaction is higher, and yield is generally lower.
(3) summary of the invention
The objective of the invention is to overcome the shortcoming of prior art, provide that a kind of technology is reasonable, reaction yield is high, catalyst levels can make things convenient for again less that recovery set is low with, production cost, environmental protection 1,2,3, the chemical synthesis process of 4-tetrazole compound.
Of the present invention 1,2,3, the 4-tetrazole compound is the tautomerism compound shown in the formula (I),
R wherein
1Be C
1～C
18Saturated alkyl or the substituting group shown in general formula (II)～(VII),
R wherein
2For one of following: hydrogen, methyl, ethyl, propyl group, butyl, chlorine, bromine, iodine, amido, hydroxyl;
Chemical synthesis process of the present invention comprises following sequential steps:
(1) provide trifluoromethanesulfonic acid zinc water-soluble solution A, will suc as formula the sodiumazide shown in nitrile shown in (VIII) and the formula (IX) in above-mentioned solution A, under 50～100 ℃, react reaction solution;
(2) step (1) gained reaction solution is added the acid neutralization, filter to such an extent that filter cake is a product, filtrate is solution B;
(VIII)R
1-CN (IX)NaN
3
Formula (VIII) R
1Define the same
The reaction formula of described reaction is as follows:
The molar ratio of described nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1.0～4.0: 0.02～1.0, be preferably 1: 1.0～2.0: 0.1～and 1.0; The weight ratio of described water and nitrile is 2～50: 1, is preferably 10～30: 1.
The reaction times is preferably 1-24 hour in the above-mentioned synthetic method, more preferably 4～24 hours.
When described reactant nitrile is solid, then when adding acid neutralizing filter, unreacted completely nitrile can to remain in filter cake be in the middle of the product, to influence degree of purity of production.As of the present invention preferred, in step (1), also described reaction solution is filtered to remove unreacted reactant completely.
Above-mentioned 1,2,3, the chemical synthesis process of 4-tetrazole compound, preferably carry out as follows: molar ratio is that 1: 1.0～2.0: 0.1～1.0 nitrile, sodiumazide, trifluoromethanesulfonic acid zinc join in the water of 10～30 times of nitrile quality, is warmed up to 50～100 ℃ of reactions 4～24 hours, filters, filtrate is neutralized to pH=5～6 with hydrochloric acid, filters to such an extent that filter cake is a product.
Recyclable the applying mechanically of catalyzer that the present invention is used, recoverying and utilizing method is: the solution B described in the step (2) directly is used as the solution A described in the step (1).
Chemical synthesis process of the present invention compared with prior art, beneficial effect is embodied in:
1. reaction yield height (generally more than 80%), production cost are low;
2. operational path advanced person, reaction conditions gentleness;
3. catalyst levels is few and recyclablely apply mechanically, do not have substantially the three wastes.
4. water can be avoided using of organic solvent to greatest extent as solvent and pollute.
(4) embodiment
The invention will be further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited to this.
Embodiment 1
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.
In thermometer, reflux condensing tube and churned mechanically 150ml four-hole boiling flask are housed, add entry 100g, benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 3.63g (10mmol) is heated to backflow (100 ℃), refluxes 4 hours.Reaction finishes, and is cooled to room temperature, is neutralized to pH=5 with concentrated hydrochloric acid.Filter, collect the white solid of being separated out, get 5-phenyl-1H-tetrazole 13.4g, yield 90%, purity 98.2%, 215 ℃ of fusing points.
Embodiment 2
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 36.3g (0.1mol), temperature of reaction is 90 ℃.
Other gets 5-phenyl-1H-tetrazole 14.1g, yield 95%, purity 98.3%, 215 ℃ of fusing points with embodiment 1.
Embodiment 3
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.5, and nitrile is a benzonitrile, and water consumption is 30 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 18.2g (50mmol), the reaction times is 6 hours.
Other gets 5-phenyl-1H-tetrazole 13.8g, yield 93%, purity 98.5%, 215 ℃ of fusing points with embodiment 1.
Embodiment 4
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.1, and nitrile is a benzonitrile, and water consumption is 20 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 13g (0.2mmol), trifluoromethanesulfonic acid zinc 3.63g (10mmol).Reaction times is 8 hours.
Other gets 5-phenyl-1H-tetrazole 12.7g, yield 85%, purity 97.8%, 215 ℃ of fusing points with embodiment 1.
Embodiment 5
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 4: 0.02, and nitrile is a benzonitrile, and water consumption is 50 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 26g (0.4mol), trifluoromethanesulfonic acid zinc 3.63g (10mmol).
Other gets 5-phenyl-1H-tetrazole 13.2g, yield 89%, purity 98.2%, 215 ℃ of fusing points with embodiment 1
Embodiment 6
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.6; Nitrile is a p-Nitrobenzyl Cyanide, and consumption is 14.8g (0.1mol); Water consumption is 20 times of nitrile quality.Reaction times is 15 hours.
Other gets 5-(4-nitrophenyl)-1H-tetrazole 18.1g, yield 80%, purity 84.5%, 220 ℃ of fusing points with embodiment 1.
Embodiment 7
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.3; Nitrile is the beta-cyano naphthalene, and consumption is 15.3g (0.1mol); Water consumption is 10 times of nitrile quality.
Other gets 5-(2-naphthyl)-1H-tetrazole 18.6g, yield 81%, purity 85.5%, 204 ℃ of fusing points with embodiment 1.
Embodiment 8
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is a p-Nitrobenzyl Cyanide, and consumption is 14.8g (0.1mol); Water consumption is 30 times of nitrile quality.
Other gets 5-(4-nitrophenyl)-1H-tetrazole 17.9g, yield 81%, purity 86.4%, 220 ℃ of fusing points with embodiment 1.
Embodiment 9
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 3: 0.4; Nitrile is an acetonitrile, and consumption is 4.1g (0.1mol); Water consumption is 40 times of nitrile quality.
Other gets 5-methyl isophthalic acid H-tetrazole 6.6g, yield 78%, purity 99.0%, 146 ℃ of fusing points with embodiment 1.
Embodiment 10
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is the 2-cyanopyridine, and consumption is 10.4g (0.1mol); Water consumption is 20 times of nitrile quality.
Other gets 5-(2-pyridyl)-1H-tetrazole 12.3g, yield 82%, purity 98.3%, 211 ℃ of fusing points with embodiment 1.
Embodiment 11
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.5; Nitrile is a lauronitrile, and consumption is 18.1 (0.1mol); Water consumption is 20 times of nitrile quality, and temperature of reaction is 70 ℃.
Other gets 5-undecyl-1H-tetrazole 17.1g, yield 75%, purity 98.1%, 206 ℃ of fusing points with embodiment 1.
Embodiment 12
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.
In thermometer, reflux condensing tube and churned mechanically 150ml four-hole boiling flask are housed, add entry 100g, benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 3.63g (10mmol) is heated to backflow (100 ℃), refluxes 4 hours.Reaction finishes, and is cooled to room temperature, filters, and removes unreacted raw material nitrile, and the filtrate water layer is neutralized to pH=5 with concentrated hydrochloric acid.Filter, collect the white solid of being separated out, get 5-phenyl-1H-tetrazole 13.14g, yield 90%, purity 99.6%, 215 ℃ of fusing points.
Embodiment 13
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 36.3g (0.1mol).
Other gets 5-phenyl-1H-tetrazole 13.9g, yield 95%, purity 99.7%, 215 ℃ of fusing points with embodiment 12.
Embodiment 14
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.5, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 6.5g (0.1mol), trifluoromethanesulfonic acid zinc 18.2g (50mmol).
Other gets 5-phenyl-1H-tetrazole 13.6g, yield 93%, purity 99.5%, 215 ℃ of fusing points with embodiment 12.
Embodiment 15
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 13g (0.2mmol), trifluoromethanesulfonic acid zinc 3.63g (10mmol).
Other gets 5-phenyl-1H-tetrazole 14.2g, yield 97%, purity 99.8%, 215 ℃ of fusing points with embodiment 12.
Embodiment 16
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 4: 0.1, and nitrile is a benzonitrile, and water consumption is 10 times of nitrile quality.Benzonitrile 10.3g (0.1mol), sodiumazide 26g (0.4mol), trifluoromethanesulfonic acid zinc 3.63g (10mmol).
Other gets 5-phenyl-1H-tetrazole 14.3g, yield 98%, purity 99.7%, 215 ℃ of fusing points with embodiment 12
Embodiment 17
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is a p-Nitrobenzyl Cyanide, and consumption is 14.8g (0.1mol); Water consumption is 10 times of nitrile quality.Reaction times is 2 hours.
Other gets 5-(4-nitrophenyl)-1H-tetrazole 17.6g, yield 92%, purity 99.7%, 220 ℃ of fusing points with embodiment 12.
Embodiment 18
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.1; Nitrile is the beta-cyano naphthalene, and consumption is 15.3g (0.1mol); Water consumption is 10 times of nitrile quality.
Other gets 5-(2-naphthyl)-1H-tetrazole 17.8g, yield 91%, purity 99.7%, 204 ℃ of fusing points with embodiment 12.
Embodiment 19
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 3: 0.1; Nitrile is an acetonitrile, and consumption is 4.1g (0.1mol); Water consumption is 10 times of nitrile quality.Reaction times is 1 hour.
Other gets 5-methyl isophthalic acid H-tetrazole 6.72g, yield 80%, purity 99.1%, 146 ℃ of fusing points with embodiment 12.
Embodiment 20
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.1; Nitrile is positive caprylic nitrile, and consumption is 12.5 (10mmol); Water consumption is 10 times of nitrile quality.Reaction times is 24 hours.
Other gets 5-heptyl-1H-tetrazole 13.3g, yield 78%, purity 99.2%, 36 ℃ of fusing points with embodiment 12.
Embodiment 21
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0..02; Nitrile is the 2-cyanopyridine, and consumption is 10.4g (0.1mol); Water consumption is 10 times of nitrile quality.
Other gets 5-(2-pyridyl)-1H-tetrazole 13.5g, yield 92%, purity 99.0%, 211 ℃ of fusing points with embodiment 12.
Embodiment 22
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is a 2-cyano group furans, and consumption is 9.3g (0.1mol); Water consumption is 10 times of nitrile quality.Reaction times is 10 hours.
Other gets 5-(2-furyl)-1H-tetrazole 13.4g, yield 88%, purity 99.6%, 166 ℃ of fusing points with embodiment 12.
Embodiment 23
Water consumption is 20 times of nitrile quality.
Other gets 5-phenyl-1H-tetrazole 13g, yield 89%, purity 99.5%, 215 ℃ of fusing points with embodiment 12.
Embodiment 24
Water consumption is 40 times of nitrile quality.
Other gets 5-phenyl-1H-tetrazole 12.8g, yield 88%, purity 99.8%, 215 ℃ of fusing points with embodiment 12.
Embodiment 25
Temperature of reaction is 50 ℃.
Other gets 5-phenyl-1H-tetrazole 11.7g, yield 80%, purity 99.5%, 215 ℃ of fusing points with embodiment 12.
Embodiment 26
Temperature of reaction is 70 ℃.
Other gets 5-phenyl-1H-tetrazole 12.3g, yield 84%, purity 99.1%, 215 ℃ of fusing points with embodiment 12.
Embodiment 27
Temperature of reaction is 90 ℃.
Other gets 5-phenyl-1H-tetrazole 12.7g, yield 87%, purity 99.3%, 215 ℃ of fusing points with embodiment 12.
Embodiment 28
Reaction times is 12 hours.
Other gets 5-phenyl-1H-tetrazole 13.4g, yield 92%, purity 99.4%, 215 ℃ of fusing points with embodiment 12.
Embodiment 29
Reaction times is 24 hours.
Other gets 5-phenyl-1H-tetrazole 13.7g, yield 94%, purity 99.6%, 215 ℃ of fusing points with embodiment 12.
Embodiment 30
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is a lauronitrile, and consumption is 18.1 (0.1mol); Water consumption is 20 times of nitrile quality, and temperature of reaction is 70 ℃.
Other gets 5-undecyl-1H-tetrazole 16.8g, yield 75%, purity 99.5%, 206 ℃ of fusing points with embodiment 12.
Embodiment 31
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.5; Nitrile is to the benzyl chloride nitrile, and consumption is 13.8g (0.1mol); Water consumption is 15 times of nitrile quality.
Other gets 5-(4-chloro-phenyl-)-1H-tetrazole 15.0g, yield 83%, purity 99.1%, fusing point 247-248 ℃ with embodiment 1.
Embodiment 32
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1: 0.1; Nitrile is a 2-chloro-3-cyanopyridine, and consumption is 13.8g (0.1mol); Water consumption is 20 times of nitrile quality.
Other gets 5-[3-(2-chlorine)-pyridyl with embodiment 12]-1H-tetrazole 12.7g, yield 70%, purity 99.4%, fusing point 219-221 ℃.
Embodiment 33
The molar ratio of nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 2: 0.2, and nitrile is a 2 thiophene acetonitrile, and consumption is 12.4g (0.1mol); Water consumption is 20 times of nitrile quality.
Other gets 5-(2-thenyl)-1H-tetrazole 13.5g, yield 81%, purity 99.6%, fusing point 204-207 ℃ with embodiment 12.
Claims (10)
1, a kind of suc as formula 1,2,3 shown in (I), the chemical synthesis process of 4-tetrazole compound,
R wherein
1Be C
1～C
18Saturated alkyl or the substituting group shown in general formula (II)～(VII),
R wherein
2For one of following: hydrogen, methyl, ethyl, propyl group, butyl, chlorine, bromine, iodine, amido, hydroxyl;
It is characterized in that comprising following sequential steps:
(1) provide trifluoromethanesulfonic acid zinc water-soluble solution A, will suc as formula the sodiumazide shown in nitrile shown in (VIII) and the formula (IX) in above-mentioned solution A, under 50～100 ℃, react reaction solution;
(2) step (1) gained reaction solution is added the acid neutralization, filter to such an extent that filter cake is a product, filtrate is solution B;
(VIII) R
1-CN (IX) NaN
3
Formula (VIII) R
1Define the same.
2, by the described chemical synthesis process of claim 1, the mol ratio that it is characterized in that described nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1.0～4.0: 0.02～1.0.
3, by the described chemical synthesis process of claim 2, the weight ratio that it is characterized in that described water and nitrile is 2～50: 1.
4,, it is characterized in that described step (1) also filters described reaction solution by the described chemical synthesis process of claim 3.
5, by one of claim 2～4 described chemical synthesis process, the mol ratio that it is characterized in that described nitrile, sodiumazide, trifluoromethanesulfonic acid zinc is 1: 1.0～2.0: 0.1～1.0.
6, by the described chemical synthesis process of claim 5, the weight ratio that it is characterized in that described water and nitrile is 10～30: 1.
7, by one of claim 1～4 described chemical synthesis process, it is characterized in that the reaction times is 1～24 hour.
8, by the described chemical synthesis process of claim 7, it is characterized in that the reaction times is 4～24 hours.
9, by one of claim 1～4 described chemical synthesis process, the solution B that it is characterized in that step (2) filtration gained is as the solution A described in the step (1).
10. by the described chemical synthesis process of claim 8, it is characterized in that: mol ratio is that 1: 1.0～2.0: 0.1～1.0 nitrile, sodiumazide, trifluoromethanesulfonic acid zinc join in the water that quality is 10～30 times of nitriles, be warmed up to 50～100 ℃ of reactions 4～24 hours, filter, filtrate is neutralized to pH=5～6 with hydrochloric acid, filters to such an extent that filter cake is a product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410052775XA CN1304381C (en) | 2004-07-09 | 2004-07-09 | Chemical synthesis method of 1,2,3,4-tetra nitroazole kind compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200410052775XA CN1304381C (en) | 2004-07-09 | 2004-07-09 | Chemical synthesis method of 1,2,3,4-tetra nitroazole kind compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1718574A true CN1718574A (en) | 2006-01-11 |
| CN1304381C CN1304381C (en) | 2007-03-14 |
Family
ID=35930533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB200410052775XA Expired - Fee Related CN1304381C (en) | 2004-07-09 | 2004-07-09 | Chemical synthesis method of 1,2,3,4-tetra nitroazole kind compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1304381C (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100591674C (en) * | 2008-02-21 | 2010-02-24 | 南京大学 | Method for catalytic synthesis of 5-substituted tetrazole by tungstate |
| CN101857577A (en) * | 2010-04-27 | 2010-10-13 | 盐城市康乐化工有限公司 | Method for preparing tetrazole compound by taking core-shell magnetic nanoparticles as catalyst |
| CN102786487A (en) * | 2012-09-03 | 2012-11-21 | 盐城工学院 | Application of graphene in preparation of tetrazole compound as catalyst |
| CN103351353A (en) * | 2013-07-25 | 2013-10-16 | 浙江海蓝化工有限公司 | Aqueous phase synthesis method of 5-methyl tetrazole |
| CN105237490A (en) * | 2015-11-16 | 2016-01-13 | 江苏恒祥化工有限责任公司 | Synthesis method of 5-methyl tetrazole |
| CN106905254A (en) * | 2017-02-20 | 2017-06-30 | 衢州学院 | A kind of preparation method of 5 phenyl 1H tetrazoles |
| CN107602495A (en) * | 2017-10-13 | 2018-01-19 | 盐城工学院 | A kind of method for preparing chiral amino acid tetrazole compound |
| CN108358863A (en) * | 2018-03-08 | 2018-08-03 | 湖北佰智昂生物化工有限公司 | A kind of method that zinc lewis acid Surfactant-Catalyzed prepares 5 '-substituted tetrazole compounds |
| CN108440433A (en) * | 2018-03-01 | 2018-08-24 | 湖北佰智昂生物化工有限公司 | The method that copper lewis acid Surfactant-Catalyzed prepares chlorination -3- substitution -2,5- diphenyltetrazolium bromides |
| CN108864157A (en) * | 2018-08-14 | 2018-11-23 | 江苏科技大学 | A kind of fluorescent probe molecule and the preparation method and application thereof for metal ion detection |
| CN109503505A (en) * | 2019-01-09 | 2019-03-22 | 浙江工业大学 | A kind of synthetic method of 5- substituted tetrazole class compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097479A (en) * | 1977-03-11 | 1978-06-27 | Miles Laboratories, Inc. | Synthesis of 5-substituted tetrazoles |
| US5502191A (en) * | 1993-07-01 | 1996-03-26 | American Cyanamid Company | Method of synthesizing sterically hindered 5-substituted-1H-tetrazoles from nitriles using a lewis acid and an azide |
| CN1189158A (en) * | 1995-05-26 | 1998-07-29 | 中国化药株式会社 | Novel reagent for tetrazole synthesis and process for producing tetrazoles therewith |
| JP3521304B2 (en) * | 1996-03-21 | 2004-04-19 | 東洋化成工業株式会社 | Method for producing 1- (tetrazolylbiphenylmethyl) imidazole derivative |
-
2004
- 2004-07-09 CN CNB200410052775XA patent/CN1304381C/en not_active Expired - Fee Related
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100591674C (en) * | 2008-02-21 | 2010-02-24 | 南京大学 | Method for catalytic synthesis of 5-substituted tetrazole by tungstate |
| CN101857577A (en) * | 2010-04-27 | 2010-10-13 | 盐城市康乐化工有限公司 | Method for preparing tetrazole compound by taking core-shell magnetic nanoparticles as catalyst |
| CN101857577B (en) * | 2010-04-27 | 2012-07-04 | 盐城市康乐化工有限公司 | Method for preparing tetrazole compound by taking core-shell magnetic nanoparticles as catalyst |
| CN102786487A (en) * | 2012-09-03 | 2012-11-21 | 盐城工学院 | Application of graphene in preparation of tetrazole compound as catalyst |
| CN102786487B (en) * | 2012-09-03 | 2014-04-30 | 盐城工学院 | Application of graphene in preparation of tetrazole compound as catalyst |
| CN103351353A (en) * | 2013-07-25 | 2013-10-16 | 浙江海蓝化工有限公司 | Aqueous phase synthesis method of 5-methyl tetrazole |
| CN105237490A (en) * | 2015-11-16 | 2016-01-13 | 江苏恒祥化工有限责任公司 | Synthesis method of 5-methyl tetrazole |
| CN106905254B (en) * | 2017-02-20 | 2019-04-16 | 衢州学院 | A kind of preparation method of 5- phenyl -1H- tetrazole |
| CN106905254A (en) * | 2017-02-20 | 2017-06-30 | 衢州学院 | A kind of preparation method of 5 phenyl 1H tetrazoles |
| CN107602495A (en) * | 2017-10-13 | 2018-01-19 | 盐城工学院 | A kind of method for preparing chiral amino acid tetrazole compound |
| CN108440433A (en) * | 2018-03-01 | 2018-08-24 | 湖北佰智昂生物化工有限公司 | The method that copper lewis acid Surfactant-Catalyzed prepares chlorination -3- substitution -2,5- diphenyltetrazolium bromides |
| CN108440433B (en) * | 2018-03-01 | 2021-02-23 | 湖北佰智昂生物化工有限公司 | Method for preparing chlorinated-3-substituted-2, 5-diphenyl tetrazole by catalysis of copper Lewis acid surfactant |
| CN108358863A (en) * | 2018-03-08 | 2018-08-03 | 湖北佰智昂生物化工有限公司 | A kind of method that zinc lewis acid Surfactant-Catalyzed prepares 5 '-substituted tetrazole compounds |
| CN108864157A (en) * | 2018-08-14 | 2018-11-23 | 江苏科技大学 | A kind of fluorescent probe molecule and the preparation method and application thereof for metal ion detection |
| CN109503505A (en) * | 2019-01-09 | 2019-03-22 | 浙江工业大学 | A kind of synthetic method of 5- substituted tetrazole class compound |
| CN109503505B (en) * | 2019-01-09 | 2020-07-21 | 浙江工业大学 | Synthesis method of 5-substituted tetrazole compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1304381C (en) | 2007-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1304381C (en) | Chemical synthesis method of 1,2,3,4-tetra nitroazole kind compound | |
| CN1170425A (en) | Heterospiro-compounds and their use as electroluminescent materials | |
| CN1273465C (en) | Method for preparing pyrimidinone compound and pharmaceutically acceptable salts thereof | |
| CN1019972C (en) | Process of preparing 5,6-dihydroxyindoles and 3-alkyl derivatives and intermediate compounds | |
| CN1665773A (en) | Process for the preparation of i n /i -monosubstituted beta-amino alcohols | |
| CN1057835A (en) | By the method for diketo-piperazine production aspartyl-phenylalanine methyl ester and new intermediate and derivative thereof | |
| CN1931839A (en) | Synthesis process of N-substituted pyrrole | |
| CN1847218A (en) | Hydroxynaphthalenedicarboxylic acid hydrazide and derivatives thereof as well as process for preparing them | |
| CN1275934C (en) | Process for the production of 1, 5-naphthalenediamine | |
| CN1533378A (en) | Process for production of quinazolines | |
| CN1094398A (en) | Be used to prepare 5-(substituent methyl)-2,5 of 3-pyridine dicarboxylic acid class, 6-two replacement-3-picolyl ammonium halide compounds | |
| CN1803777A (en) | Chemical synthesis method of pyrimidine thioketone | |
| CN1247556C (en) | Process for producing dibenzothiazepine derivatives | |
| CN1138027A (en) | Nitric esters from derivatives of 2-(2,6-dihalophenylamino) phenylacetoxyacetic acid and their preparation procedures | |
| CN1261420C (en) | Process for the manufacture of thiazole derivativs with pesticide activity | |
| CN1787998A (en) | Method for producing bipyridinium compound | |
| CN100339360C (en) | Process for producing aromatic nitrile compound | |
| CN1217946C (en) | Process for preparing pyrazolopyrimidinone derivatives for treatment of impotence | |
| CN1711245A (en) | Process for the preparation of 2-aminomethylpyridine derivative | |
| CN1027260C (en) | Process for preparing acyl cyanides in anhydrous medium | |
| CN1102925C (en) | Bis-(aminocarbonylnaphthol) derivatives | |
| CN1178919C (en) | Synthesis of intermediates useful in preparing tricyclic compounds | |
| CN1915956A (en) | Chemical method for synthesizing palmitoyl chloride | |
| CN1552685A (en) | Environmental protection cleaning process method for producing high-purity orthoformate | |
| CN1235891C (en) | Process for producing substituted alkylamine derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |