CN102442962A - Production method of 1-alkyl tetrazole - Google Patents
Production method of 1-alkyl tetrazole Download PDFInfo
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- CN102442962A CN102442962A CN2010105371599A CN201010537159A CN102442962A CN 102442962 A CN102442962 A CN 102442962A CN 2010105371599 A CN2010105371599 A CN 2010105371599A CN 201010537159 A CN201010537159 A CN 201010537159A CN 102442962 A CN102442962 A CN 102442962A
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- tetrazole
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- alkyl tetrazole
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Abstract
The invention discloses a production method of 1-alkyl tetrazole. The production method is characterized in that tetrazole and dialkyl carbonate carry out a reflux reaction in a solvent in the presence of a weakly basic catalyst to generate 1-alkyl tetrazole and 1-alkyl 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-alkyl tetrazole production technique; Like 1-methyl tetrazole: ZhurnalOrganicheskoi 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 Communicatiohs, (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-alkyl tetrazole that yield is high.
Technical solution of the present invention is:
The working method of 1-alkyl tetrazole, its characteristic: in weakly alkaline catalyzer, solvent, under the back flow reaction condition, react generation 1-alkyl base tetrazole, reaction formula by tetrazole and dialkyl carbonate:
R wherein is CH3-or CH3CH2-or CH3CH2CH2-or
Reaction is under the reflux condition, to carry out.The weakly alkaline catalyzer is meant: yellow soda ash, salt of wormwood, sodium hydrogencarbonate, saleratus; Solvent is meant: the alcoholic solvent of THF, 2-methyltetrahydrofuran, N, toluene, benzene, C1-10.The mol ratio of tetrazole, methylcarbonate, catalyzer, solvent is: tetrazole: dialkyl carbonate: 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 described further:
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 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 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%).
Embodiment 5:
1 mole tetrazole, 1.5 moles carbonic acid diisopropyl ester, 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 obtains product, with refining product 1-sec.-propyl tetrazole 71 grams (yield 62.8%) that obtain of ethanol.
Claims (5)
1. the working method of a 1-alkyl tetrazole is characterized in that: in weakly alkaline catalyzer, solvent under the back flow reaction condition, reaction generates 1-alkyl tetrazole, reaction formula by tetrazole and dialkyl carbonate:
R wherein is CH3-or CH3CH2-or CH3CH2CH2-or
2. the working method of 1-alkyl tetrazole according to claim 1 is characterized in that: reaction is to reflux being heated under 100-140 ℃ the condition.
3. the working method of 1-alkyl tetrazole according to claim 1 and 2 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-alkyl 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-alkyl tetrazole according to claim 1 is characterized in that: the mol ratio of tetrazole, dialkyl carbonate, catalyzer, solvent is: tetrazole: dialkyl carbonate: catalyzer: solvent=1: 0.6～20: 0.6～20: 2～100.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105371599A CN102442962A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-alkyl tetrazole |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105371599A CN102442962A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-alkyl tetrazole |
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| CN102442962A true CN102442962A (en) | 2012-05-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2010105371599A Pending CN102442962A (en) | 2010-11-10 | 2010-11-10 | Production method of 1-alkyl tetrazole |
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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 |
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2010
- 2010-11-10 CN CN2010105371599A patent/CN102442962A/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 |
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Application publication date: 20120509 |