CN1562981A - Method for fabricating halogenation linear chain paraffin tetrazole - Google Patents
Method for fabricating halogenation linear chain paraffin tetrazole Download PDFInfo
- Publication number
- CN1562981A CN1562981A CN 200410014469 CN200410014469A CN1562981A CN 1562981 A CN1562981 A CN 1562981A CN 200410014469 CN200410014469 CN 200410014469 CN 200410014469 A CN200410014469 A CN 200410014469A CN 1562981 A CN1562981 A CN 1562981A
- Authority
- CN
- China
- Prior art keywords
- tetrazole
- tetrahydrofuran
- thf
- chain paraffin
- halo
- 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.)
- Pending
Links
Landscapes
- Plural Heterocyclic Compounds (AREA)
Abstract
This invention relates to 5-halogenated straight-chain paraffic tetrazole prodn. method. Halogenated cyanogen, sodium azide and tetrahydrofuran react in the presence of aluminium trichloride. This invention has advantages of: simple prodn. process, easy to operate, high product yield of 51-82%.
Description
Technical field:
The present invention relates to a kind of preparation method of nitrogen-containing heterocycle compound.
Background technology:
Existing 5-halo straight-chain paraffin tetrazole is produced, and is to be that starting raw material obtains through cyclization, chlorination with the hydroxyalkyl nitrile, complex process, and yield is low.
Summary of the invention:
The object of the present invention is to provide a kind of technology simple, the production method of the 5-halo straight-chain paraffin tetrazole that yield is high.
Technical solution of the present invention is:
A kind of production method of 5-halo straight-chain paraffin tetrazole, its feature: under the condition that aluminum chloride exists, reaction generates 5-halo straight-chain paraffin tetrazole, reaction formula by halo nitrile and sodiumazide, tetrahydrofuran (THF):
R=Cl or Br, n=1～8.
Reaction is to carry out under the reflux condition.The mol ratio of halo nitrile and tetrahydrofuran (THF), aluminum chloride, sodiumazide is: halo nitrile: tetrahydrofuran (THF): aluminum chloride: sodiumazide=1: 18～35: 0.8～2.5: 0.8～6.
Technology of the present invention is simple, and is easy to operate, and the product yield height reaches 51～82%.
The invention will be further described below in conjunction with embodiment:
Embodiment:
Embodiment 1:
Chloromethyl cyanide, tetrahydrofuran (THF), sodiumazide, aluminum chloride are mixed, under the reflux condition, react 12～72 hours (can be 12,24,36,48,60,72 hours), generate the 5-5-chloromethyl tetrazole, reaction formula:
The mol ratio of chloromethyl cyanide and tetrahydrofuran (THF), aluminum chloride, sodiumazide is: chloromethyl cyanide: tetrahydrofuran (THF): aluminum chloride: sodiumazide=1: 18～35: 0.8～2.5: 0.8～6 (example 1: 18: 1: 4,1: 25: 2.5: 3,1: 35: 1.8: 1,1: 25: 2: 6).When being cooled to below 20 ℃ (20,15,10,5 ℃ of examples), add hydrochloric acid and transfer PH to 2～4 (example 2,3,4), layering, get the tetrahydrofuran (THF) layer, and use anhydrous sodium sulfate drying, behind the pressure reducing and steaming solvent, add chloride alkane-chloroform (or tetracol phenixin, ethylene dichloride) and carry out recrystallization, product 5-5-chloromethyl tetrazole, molar yield in chloromethyl cyanide greater than 74%.
Embodiment 2:
Chloroethyl nitrile, tetrahydrofuran (THF), sodiumazide, aluminum chloride are mixed, under the reflux condition, react 12～72 hours (can be 12,24,36,48,60,72 hours), generate 5-chloroethyl tetrazole, reaction formula:
The mol ratio of chloroethyl nitrile and tetrahydrofuran (THF), aluminum chloride, sodiumazide is: chloroethyl nitrile: tetrahydrofuran (THF): aluminum chloride: sodiumazide=1: 18～35: 0.8～2.5: 0.8～6 (example 1: 18: 1: 4,1: 25: 2.5: 3,1: 35: 1.8: 1,1: 25: 2: 6).When being cooled to below 20 ℃ (20,15,10,5 ℃ of examples), add hydrochloric acid and transfer PH to 2～4 (example 2,3,4), layering, get the tetrahydrofuran (THF) layer, and use anhydrous sodium sulfate drying, behind the pressure reducing and steaming solvent, add chloride alkane-ethylene dichloride (or chloroform, tetracol phenixin) and carry out recrystallization, product, molar yield in chloroethyl nitrile greater than 81%.
Embodiment 3:
Bromopropionitrile, tetrahydrofuran (THF), sodiumazide, aluminum chloride are mixed, under the reflux condition, react 12～72 hours (can be 12,24,36,48,60,72 hours), generate 5-bromotrifluoromethane tetrazole, reaction formula:
The mol ratio of bromopropionitrile and tetrahydrofuran (THF), aluminum chloride, sodiumazide is: bromopropionitrile: tetrahydrofuran (THF): aluminum chloride: sodiumazide=1: 18～35: 0.8～2.5: 0.8～6 (example 1: 18: 1: 4,1: 25: 2.5: 3,1: 35: 1.8: 1,1: 25: 2: 6).When being cooled to below 20 ℃ (20,15,10,5 ℃ of examples), add hydrochloric acid and transfer PH to 2～4 (example 2,3,4), layering, get the tetrahydrofuran (THF) layer, and use anhydrous sodium sulfate drying, behind the pressure reducing and steaming solvent, add chloride alkane-tetracol phenixin (or chloroform, ethylene dichloride) and carry out recrystallization, product, molar yield in bromopropionitrile greater than 51%.
Reaction raw materials chloromethyl cyanide among the embodiment 1 is substituted with chlorobutyronitrile or chlorine heptonitrile, chlorine caprylic nitrile, chlorine valeronitrile, the own nitrile of chlorine, chlorine pelargonitrile, bromine butyronitrile, bromine heptonitrile, bromine caprylic nitrile, bromine valeronitrile, the own nitrile of bromine, bromine pelargonitrile, generate corresponding 5-halo straight-chain paraffin tetrazole, steps such as remaining reaction condition, consumption, product recovery form new embodiment again all with embodiment 1.
Claims (3)
1, a kind of production method of 5-halo straight-chain paraffin tetrazole is characterized in that: under the condition that aluminum chloride exists, reaction generates 5-halo straight-chain paraffin tetrazole, reaction formula by halo nitrile and sodiumazide, tetrahydrofuran (THF):
R=Cl or Br, n=1～8.
2, the production method of 5-halo straight-chain paraffin tetrazole according to claim 1, it is characterized in that: reaction is to carry out under the reflux condition.
3, the production method of 5-halo straight-chain paraffin tetrazole according to claim 1 and 2, it is characterized in that: the mol ratio of halo nitrile and tetrahydrofuran (THF), aluminum chloride, sodiumazide is: halo nitrile: tetrahydrofuran (THF): aluminum chloride: sodiumazide=1: 18～35: 0.8～2.5: 0.8～6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410014469 CN1562981A (en) | 2004-03-24 | 2004-03-24 | Method for fabricating halogenation linear chain paraffin tetrazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410014469 CN1562981A (en) | 2004-03-24 | 2004-03-24 | Method for fabricating halogenation linear chain paraffin tetrazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1562981A true CN1562981A (en) | 2005-01-12 |
Family
ID=34478387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410014469 Pending CN1562981A (en) | 2004-03-24 | 2004-03-24 | Method for fabricating halogenation linear chain paraffin tetrazole |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1562981A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101805306A (en) * | 2010-04-29 | 2010-08-18 | 南通市华峰化工有限责任公司 | Production method of 5-chloromethyl tetrazole or 5-chloroethyl tetrazole |
| CN101812029A (en) * | 2010-04-29 | 2010-08-25 | 南通市华峰化工有限责任公司 | Method for producing 5-halogenolinear alkyl tetrazole |
| CN102906075A (en) * | 2010-03-12 | 2013-01-30 | 拜耳知识产权有限责任公司 | Process for the preparation of 5-substituted 1-alkyltetrazoles |
-
2004
- 2004-03-24 CN CN 200410014469 patent/CN1562981A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102906075A (en) * | 2010-03-12 | 2013-01-30 | 拜耳知识产权有限责任公司 | Process for the preparation of 5-substituted 1-alkyltetrazoles |
| CN102906075B (en) * | 2010-03-12 | 2016-01-13 | 拜耳知识产权有限责任公司 | The preparation method of the 1-alkyl tetrazolium that 5-replaces |
| CN101805306A (en) * | 2010-04-29 | 2010-08-18 | 南通市华峰化工有限责任公司 | Production method of 5-chloromethyl tetrazole or 5-chloroethyl tetrazole |
| CN101812029A (en) * | 2010-04-29 | 2010-08-25 | 南通市华峰化工有限责任公司 | Method for producing 5-halogenolinear alkyl tetrazole |
| CN101812029B (en) * | 2010-04-29 | 2012-02-15 | 南通市华峰化工有限责任公司 | Method for producing 5-halogenolinear alkyl tetrazole |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101031529A (en) | Chemical production processes and systems | |
| JP2010189372A5 (en) | ||
| CN101041622A (en) | Preparation method of memantine salt | |
| CN108840854B (en) | Method for synthesizing 5-chlorothiophene-2-carboxylic acid by one-pot method | |
| CN104003863B (en) | A kind of benzoic green synthesis method | |
| CN105061535A (en) | Synthetic method of sofosbuvir intermediate | |
| CN1562981A (en) | Method for fabricating halogenation linear chain paraffin tetrazole | |
| CN104592013A (en) | Method for synthesizing p-fluorobenzoyl chloride | |
| CN107056590A (en) | One kind prepares and purifies the commercial run of 4,4 ' dimethoxytrityl chloromethanes | |
| CN101260084A (en) | Production technique for preparing 5-alkyltetranitrozole by high pressure method | |
| CN1277811C (en) | Process for producing bromo chloro isocyanuric acid and its use | |
| CN1903830A (en) | Preparation method of 2-bromo-2-nitro-1,3-propylene glycol | |
| CN105481639A (en) | Method for preparing biphenyl compound | |
| CN1034410C (en) | Industrial method for preparation of pure iodic acid solution and its salts | |
| CN101318686A (en) | Method for preparing by-product calcium fluoride of calcium chloride dihydrate | |
| CN101696153B (en) | Preparation method of 3,3-dimethyl-1-butanol | |
| CN1721581A (en) | Process for preparing antimonic oxychloride crystal | |
| CN1814578A (en) | Method for preparing chloromethyl substituted arene | |
| CN1390820A (en) | Process for preparing trifluomethoxybenzene | |
| JP4662649B2 (en) | Novel phosphine compounds | |
| CN1927842A (en) | Synthesis technology of 1,3-dimethyl-2-chloroimidazoline chloride | |
| CN1566063A (en) | Production process for chloroacetic acid | |
| CN1762942A (en) | A kind of preparation method for isodeca-deca-isoprene-yl alcohol | |
| CN1244674C (en) | Method for fabricating thermal stablilizer made from wool ester, rare earth in use for PVC | |
| AU2003268683B2 (en) | Process for production of an acetylenic compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |