CN102442961A - Production method of 1-methyl tetrazole - Google Patents
Production method of 1-methyl tetrazole Download PDFInfo
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- CN102442961A CN102442961A CN201010537157XA CN201010537157A CN102442961A CN 102442961 A CN102442961 A CN 102442961A CN 201010537157X A CN201010537157X A CN 201010537157XA CN 201010537157 A CN201010537157 A CN 201010537157A CN 102442961 A CN102442961 A CN 102442961A
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- tetrazole
- methyl
- solvent
- methyl tetrazole
- working method
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Abstract
The invention discloses a production method of 1-methyl tetrazole. The production method is characterized in that tetrazole and dimethyl carbonate is in the reflux reaction in a solvent in the presence of a weakly basic catalyst to generate 1-methyl tetrazole and 1-methyl tetrazole is subjected to aftertreatment to obtain the target product. The production method has the advantages of simple process, easiness in operation and high product yield, and the product yield reaches 50-82.5%.
Description
Technical field:
The present invention relates to a kind of preparation method of nitrogen-containing heterocycle compound.
Background technology:
Existing 1-methyl tetrazole is produced; As: Zhurnal Organicheskoi Khimii (1984), 20 (2), 398-404. has introduced with the adjusting refluxed reaction at acetic acid of aqueous methylamine solution, triethyl orthoformate and sodiumazide; Processing obtains 1-methyl tetrazole; This technology is used sodiumazide and acetic acid, not only blast easily, and also also very big to corrosion on Equipment property; Mendeleev Communications, (1), 10-11; 1995 grades have been introduced to be reacted under alkaline condition by tetrazole and methyl-sulfate and have been obtained 1-methyl tetrazole, use the methyl-sulfate severe toxicity in the technology.
Summary of the invention:
The object of the present invention is to provide a kind of technology simple, the working method of the 1-methyl tetrazole that yield is high.
Technical solution of the present invention is:
The working method of 1-methyl tetrazole, its characteristic: in weakly alkaline catalyzer, solvent, under the back flow reaction condition, react generation 1-methyl tetrazole, reaction formula by tetrazole and methylcarbonate:
Further, reaction is under the reflux condition, to carry out.
Further, the weakly alkaline catalyzer is meant: yellow soda ash or salt of wormwood or sodium hydrogencarbonate or saleratus.
Further, solvent is meant: the alcoholic solvent of THF or 2-methyltetrahydrofuran or N or toluene or benzene or C1-10.
Further, the mol ratio of tetrazole, methylcarbonate, catalyzer, solvent is: tetrazole: methylcarbonate: catalyzer: solvent=1: 0.6～20: 0.6～20: 2～100.
Technology of the present invention is simple, and is easy to operate, and product yield is high, reaches 50～82.5%.
Below in conjunction with embodiment the present invention is done into-goes on foot explanation:
Embodiment:
Embodiment 1:
1 mole tetrazole, 1.5 moles methylcarbonate, 1.1 moles salt of wormwood joined in 600 milliliters the N, be heated to 130 ℃ of back flow reaction 18 hours, reaction finishes the most of solvent of back pressure reducing and steaming; In debris, add 1000 ml waters; Stirred 1 hour, and, merged organic layer with 400 milliliters ethyl acetate extraction four times; Concentrating under reduced pressure desolvates; Product is collected in decompression, obtains 1-methyl tetrazole 58.5 grams (yield 69.6%), 2-methyl tetrazole 14.2 grams (yield 16.9%).
Embodiment 2:
1 mole tetrazole, 1.5 moles methylcarbonate, 1.1 moles salt of wormwood joined in 800 milliliters the toluene, heated 130 ℃ of back flow reaction 24 hours, reaction finishes the back and adds 1000 ml waters; Stirred 1 hour, layering, water layer is used 400 milliliters twice of methylbenzene extraction again; Merge organic layer, concentrating under reduced pressure desolvates, and product is collected in decompression; Obtain 1-methyl tetrazole 69.3 grams (yield 82.5%), 2-methyl tetrazole 5.2 grams (yield 6.2%).
Embodiment 3:
1 mole tetrazole, 1.5 moles methylcarbonate, 1.1 moles salt of wormwood joined in 600 milliliters the THF, be heated to 130 ℃ of back flow reaction 48 hours, reaction finishes the most of solvent of back pressure reducing and steaming; In debris, add 1000 ml waters; Stirred 1 hour, and, merged organic layer with 400 milliliters ethyl acetate extraction four times; Concentrating under reduced pressure desolvates; Product is collected in decompression, obtains 1-methyl tetrazole 58.5 grams (yield 69.6%), 2-methyl tetrazole 18.1 grams (yield 21.5%).
Embodiment 4:
1 mole tetrazole, 1.5 moles methylcarbonate, 1.1 moles yellow soda ash joined in 600 milliliters the N, be heated to 130 degree reactions 18 hours, reaction finishes the most of solvent of back pressure reducing and steaming; In debris, add 1000 ml waters; Stirred 1 hour, and, merged organic layer with 400 milliliters ethyl acetate extraction four times; Concentrating under reduced pressure desolvates; Product is collected in decompression, obtains 1-methyl tetrazole 43.5 grams (yield 51.8%), 2-methyl tetrazole 25.1 grams (yield 29.9%).
Claims (5)
1. the working method of a 1-methyl tetrazole is characterized in that: in weakly alkaline catalyzer, solvent under the back flow reaction condition, reaction generates 1-methyl tetrazole, reaction formula by tetrazole and methylcarbonate:
2. the working method of 1-methyl tetrazole according to claim 1 is characterized in that: reaction is under the reflux condition, to carry out, said Heating temperature 100-140 ℃.
3. the working method of 1-methyl tetrazole according to claim 1 is characterized in that: said weakly alkaline catalyzer is meant: yellow soda ash or salt of wormwood or sodium hydrogencarbonate or saleratus.
4. the working method of 1-methyl tetrazole according to claim 1 is characterized in that: said solvent is meant: the alcoholic solvent of THF or 2-methyltetrahydrofuran or N or toluene or benzene or C1-10.
5. the working method of 1-methyl tetrazole according to claim 1 is characterized in that: the mol ratio of tetrazole, methylcarbonate, catalyzer, solvent is: tetrazole: methylcarbonate: catalyzer: solvent=1: 0.6～20: 0.6～20: 2～100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010537157XA CN102442961A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-methyl tetrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010537157XA CN102442961A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-methyl tetrazole |
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| CN102442961A true CN102442961A (en) | 2012-05-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN201010537157XA Pending CN102442961A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-methyl tetrazole |
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| CN (1) | CN102442961A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103508972A (en) * | 2013-09-09 | 2014-01-15 | 南通市华峰化工有限责任公司 | 2-methyl-5-aminotetrazole synthesis production method |
| CN103524445A (en) * | 2013-09-09 | 2014-01-22 | 南通市华峰化工有限责任公司 | Method for synthetic production of 1-methyl-5-aminotetrazole |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1860117A (en) * | 2003-07-28 | 2006-11-08 | 詹森药业有限公司 | Benzimidazole, benzthiazole and benzoxazole derivatives and their use as lta4h modulators |
-
2010
- 2010-11-10 CN CN201010537157XA patent/CN102442961A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1860117A (en) * | 2003-07-28 | 2006-11-08 | 詹森药业有限公司 | Benzimidazole, benzthiazole and benzoxazole derivatives and their use as lta4h modulators |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103508972A (en) * | 2013-09-09 | 2014-01-15 | 南通市华峰化工有限责任公司 | 2-methyl-5-aminotetrazole synthesis production method |
| CN103524445A (en) * | 2013-09-09 | 2014-01-22 | 南通市华峰化工有限责任公司 | Method for synthetic production of 1-methyl-5-aminotetrazole |
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Application publication date: 20120509 |