CN104402820A - Synthesis method of 1-ethyl-2-methylimidazoline - Google Patents
Synthesis method of 1-ethyl-2-methylimidazoline Download PDFInfo
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- CN104402820A CN104402820A CN201410713818.8A CN201410713818A CN104402820A CN 104402820 A CN104402820 A CN 104402820A CN 201410713818 A CN201410713818 A CN 201410713818A CN 104402820 A CN104402820 A CN 104402820A
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- Prior art keywords
- ethyl
- tetrahydroglyoxaline
- methyl
- synthetic method
- zinc powder
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of 1-ethyl-2-methylimidazoline, which comprises the steps of allowing ethidene diamine to react with acetonitrile to generate 2-methylimidazoline, and allowing 2-methylimidazoline to react with bromoethane to generate 1-ethyl-2-methylimidazoline. 1-ethyl-2-methylimidazoline synthesized with the method is high in quality and purity, and the synthesis method is simple, low in energy consumption and low in cost.
Description
Technical field
The present invention relates to medicine and manufacture field, specifically a kind of synthetic method of 1-Ethyl-2-Methyl tetrahydroglyoxaline.
Background technology
1-Ethyl-2-Methyl tetrahydroglyoxaline, chemical formula is C6H12N2, molecular weight 112.17288, boiling point: 266-268 DEG C, is called for short: EMZ.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of synthetic method of 1-Ethyl-2-Methyl tetrahydroglyoxaline, and its synthetic method is simple, and yield is high.
Technical scheme of the present invention is:
A synthetic method for 1-Ethyl-2-Methyl tetrahydroglyoxaline, comprises the steps:
(1), first quadrol and sulphur are joined in reaction vessel and stir temperature rising reflux, at 100 DEG C, slowly drip acetonitrile control quantity of reflux, dropwise rear be slowly warmed up to 150-160 DEG C at reaction 1 hour, add zinc powder again, insulation reaction 2 hours after zinc powder adds, finally heat up and collect cut, collect the cut of 190-206 DEG C, i.e. glyoxal ethyline quinoline;
(2), the glyoxal ethyline quinoline that step (1) is obtained is joined in reaction vessel stir together with salt of wormwood, sodium hydroxide, and then add monobromethane stirring, at room temperature react 3 hours, add water after reacting completely stirring, layering, water layer extracts, and after organic layer merges, namely concentrating under reduced pressure obtains 1-Ethyl-2-Methyl tetrahydroglyoxaline.
In described step (1), the mass ratio of quadrol, sulphur, acetonitrile and zinc powder is 1: 0.08-0.085: 0.8-0.85: 0.17-0.18.
In described step (2), the mass ratio of glyoxal ethyline quinoline, salt of wormwood, sodium hydroxide and monobromethane is 1: 1.6-1.7: 0.9-1: 1.2-1.4.
In batches zinc powder in described step (1) adds.
In described step (1), water layer adopts chloroform extraction, repeats 3 times.
Advantage of the present invention:
The 1-Ethyl-2-Methyl tetrahydroglyoxaline quality of the present invention's synthesis is good, and purity is high, and synthetic method is simple, and less energy consumption, cost is low.
Embodiment
A synthetic method for 1-Ethyl-2-Methyl tetrahydroglyoxaline, comprises the steps:
(1), first 62g quadrol and 5.2g sulphur are joined in reaction vessel and stir temperature rising reflux, at 100 DEG C, slowly drip 6g acetonitrile control quantity of reflux, dropwise rear be slowly warmed up to 150-160 DEG C at reaction 1 hour, add 11g zinc powder more in batches, insulation reaction 2 hours after zinc powder adds, finally heat up and collect cut, collect the cut of 190-206 DEG C, i.e. glyoxal ethyline quinoline;
(2), 4.2g glyoxal ethyline quinoline is joined and stirs 1min together with 6.9g salt of wormwood, 4g sodium hydroxide in reaction vessel after, and then add 5.45g monobromethane stir, at room temperature react 3 hours, add water 20ml, stir 30min, the chloroform extraction of water layer 30ml once, repeats 3 times.Namely concentrating under reduced pressure obtains 1-Ethyl-2-Methyl tetrahydroglyoxaline, output 3.4g.
。
Claims (5)
1. a synthetic method for 1-Ethyl-2-Methyl tetrahydroglyoxaline, is characterized in that: comprise the steps:
(1), first quadrol and sulphur are joined in reaction vessel and stir temperature rising reflux, at 100 DEG C, slowly drip acetonitrile control quantity of reflux, dropwise rear be slowly warmed up to 150-160 DEG C at reaction 1 hour, add zinc powder again, insulation reaction 2 hours after zinc powder adds, finally heat up and collect cut, collect the cut of 190-206 DEG C, i.e. glyoxal ethyline quinoline;
(2), the glyoxal ethyline quinoline that step (1) is obtained is joined in reaction vessel stir together with salt of wormwood, sodium hydroxide, and then add monobromethane stirring, at room temperature react 3 hours, add water after reacting completely stirring, layering, water layer extracts, and after organic layer merges, namely concentrating under reduced pressure obtains 1-Ethyl-2-Methyl tetrahydroglyoxaline.
2. the synthetic method of a kind of 1-Ethyl-2-Methyl tetrahydroglyoxaline according to claim 1, is characterized in that: in described step (1), the mass ratio of quadrol, sulphur, acetonitrile and zinc powder is 1: 0.08-0.085: 0.8-0.85: 0.17-0.18.
3. the synthetic method of a kind of 1-Ethyl-2-Methyl tetrahydroglyoxaline according to claim 1, is characterized in that: in described step (2), the mass ratio of glyoxal ethyline quinoline, salt of wormwood, sodium hydroxide and monobromethane is 1: 1.6-1.7: 0.9-1: 1.2-1.4.
4. the synthetic method of a kind of 1-Ethyl-2-Methyl tetrahydroglyoxaline according to claim 1, is characterized in that: in batches the zinc powder in described step (1) adds.
5. the synthetic method of a kind of 1-Ethyl-2-Methyl tetrahydroglyoxaline according to claim 1, is characterized in that: in described step (1), water layer adopts chloroform extraction, repeats 3 times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410713818.8A CN104402820A (en) | 2014-12-02 | 2014-12-02 | Synthesis method of 1-ethyl-2-methylimidazoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410713818.8A CN104402820A (en) | 2014-12-02 | 2014-12-02 | Synthesis method of 1-ethyl-2-methylimidazoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104402820A true CN104402820A (en) | 2015-03-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410713818.8A Pending CN104402820A (en) | 2014-12-02 | 2014-12-02 | Synthesis method of 1-ethyl-2-methylimidazoline |
Country Status (1)
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| CN (1) | CN104402820A (en) |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08295675A (en) * | 1995-04-28 | 1996-11-12 | Tosoh Corp | Production of 2-imidazoline |
| JPH0940651A (en) * | 1995-08-01 | 1997-02-10 | Tosoh Corp | Production of 2-imidazoline compound |
| JPH10287656A (en) * | 1997-04-16 | 1998-10-27 | Tosoh Corp | Production of 2-imidazolines |
| JP3288644B2 (en) * | 1999-03-29 | 2002-06-04 | 三洋化成工業株式会社 | Method for producing N-substituted cyclic amidine |
| JP2003313172A (en) * | 2002-04-23 | 2003-11-06 | Tosoh Corp | Method for producing n-substituted imidazole |
| CN102050785A (en) * | 2010-11-29 | 2011-05-11 | 中国农业大学 | Imidazoline ionic liquid and preparation method and application thereof |
| WO2014130582A2 (en) * | 2013-02-19 | 2014-08-28 | Senomyx, Inc. | Compounds useful as modulators of trpm8 |
| CN104115245A (en) * | 2012-04-26 | 2014-10-22 | 三洋化成工业株式会社 | Electrolytic solution for aluminum electrolytic capacitor, and aluminum electrolytic capacitor using same |
-
2014
- 2014-12-02 CN CN201410713818.8A patent/CN104402820A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08295675A (en) * | 1995-04-28 | 1996-11-12 | Tosoh Corp | Production of 2-imidazoline |
| JPH0940651A (en) * | 1995-08-01 | 1997-02-10 | Tosoh Corp | Production of 2-imidazoline compound |
| JPH10287656A (en) * | 1997-04-16 | 1998-10-27 | Tosoh Corp | Production of 2-imidazolines |
| JP3288644B2 (en) * | 1999-03-29 | 2002-06-04 | 三洋化成工業株式会社 | Method for producing N-substituted cyclic amidine |
| JP2003313172A (en) * | 2002-04-23 | 2003-11-06 | Tosoh Corp | Method for producing n-substituted imidazole |
| CN102050785A (en) * | 2010-11-29 | 2011-05-11 | 中国农业大学 | Imidazoline ionic liquid and preparation method and application thereof |
| CN104115245A (en) * | 2012-04-26 | 2014-10-22 | 三洋化成工业株式会社 | Electrolytic solution for aluminum electrolytic capacitor, and aluminum electrolytic capacitor using same |
| WO2014130582A2 (en) * | 2013-02-19 | 2014-08-28 | Senomyx, Inc. | Compounds useful as modulators of trpm8 |
Non-Patent Citations (2)
| Title |
|---|
| GUOZHONG YE,等: "Push–pull alkenes by reacting N,N0-dimethyl cyclic ketene N,N0-acetals with isocyanates: synthesis, structures, and reactivities", 《TETRAHEDRON LETTERS》, vol. 50, no. 18, 25 February 2009 (2009-02-25), pages 2135 - 2139, XP026011899, DOI: doi:10.1016/j.tetlet.2009.02.160 * |
| 徐文清,等: "1,2-二甲基咪唑啉的合成及表征", 《有机化学》, vol. 29, no. 05, 15 May 2009 (2009-05-15), pages 802 - 805 * |
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Application publication date: 20150311 |