CN108250104A - A kind of synthetic method of 2- amino malononitrile - Google Patents
A kind of synthetic method of 2- amino malononitrile Download PDFInfo
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- CN108250104A CN108250104A CN201810143901.4A CN201810143901A CN108250104A CN 108250104 A CN108250104 A CN 108250104A CN 201810143901 A CN201810143901 A CN 201810143901A CN 108250104 A CN108250104 A CN 108250104A
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- Prior art keywords
- amino
- malononitrile
- synthetic method
- malonamides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of synthetic methods of 2 amino malononitrile, include the following steps：1）Using diethyl aminomalonate as starting material, the aqueous solution of 40 60w/v% ammonium chlorides is direct plungeed into, at 100 120 DEG C, 25 hours is reacted, is prepared and prepares 2 amino malonamides；2）By step 1）2 amino malonamides being prepared are dissolved in organic solvent, after heat temperature raising, add in solid phosgene, are heated to reflux 10 12h and generate 2 amino malononitrile.Simple pollution-free, safety and environmental protection of the invention, the further application for 2 amino malononitrile provide the foundation.
Description
Technical field
Present invention relates particularly to a kind of synthetic methods of 2- amino malononitrile.
Background technology
2- amino malononitrile plays an important role research origin of life, (the Roman such as Roman et
A.Motiyenko, Laurent Margules, Eugen A.Alekseev, and Jean-Claude Guillemin.High-
Resolution Millimeter Wave Spectroscopy and Ab InitioCalculations of
Aminomalononitrile；1049-1053) speculate as follows in synthetic route of the 2- amino malononitrile in interstellar matter：
In order to preferably study 2- amino malononitrile, provide fundamental basis for research astrophysics, it is necessary to first close as a result,
Into going out 2- amino malononitrile.
Invention content
It is an object of the invention to develop a kind of synthetic method of 2- aminopropionitriles.
To solve the above-mentioned problems, the technology that the present invention uses is a kind of such, synthetic method of 2- amino malononitrile,
Include the following steps：
1) using 2- diethyl aminomalonates as starting material, the aqueous solution of 40-60% ammonium chlorides is direct plungeed into, in 100-
At 120 DEG C, 2-5 hour is reacted, is prepared and prepares 2- amino malonamides；
2) the 2- amino malonamide that step 1) is prepared is heated to reflux under the conditions of solid phosgene and toluene solvant
12 hours generate 2- amino malononitrile.
The reaction equation being specifically related to is as follows：
Preferably, the molar ratio of ammonium chloride is 1 in the aqueous solution of the diethyl aminomalonate and ammonium chloride：2-3.
Preferably, the mass ratio of the 2- amino malonamide and solid phosgene is 1:1-1.5.
Preferably, the solvent is methanol, ethyl alcohol or chloroform.
Advantageous effect：Simple pollution-free, safety and environmental protection of the invention, the further application for 2- amino malononitrile provide base
Plinth.
Specific embodiment
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, the embodiment
It is only used for explaining the present invention, be not intended to limit the scope of the present invention..
Embodiment 1
Weighing 2- amidomalonic acid second fat 17.5g, 50% aqueous ammonium chloride solution 22g is heated to reflux 2 hours under 100 degree,
After reaction, it filters, heated-air drying 8 hours, obtains white 10.2g2- amino malonamide, yield 87% under 60 degree.
Embodiment 2
Weighing 2- amidomalonic acid second fat 17.5g, 30% aqueous ammonium chloride solution 37g is heated to reflux 2 hours under 100 degree,
After reaction, it filters, vacuum drying 8 hours, 7.8g 2- amino malonamides, yield 68% under 60 degree.
Embodiment 3
15 grams of 2- amino malonamide is weighed, 150 milliliters of toluene is added in, solid phosgene 15 is added portionwise under stirring
Gram, 12 hours are heated to reflux, after reaction, 20 grams of 20% sodium hydroxide is added in, excessive phosgene is quenched, and extracted with toluene
It takes, is dehydrated, and concentrate toluene layer, obtains the 2- amino malononitrile of 8.8g.
Embodiment 4
15 grams of 150 milliliters of toluene of addition of 2- amino malonamide are weighed, 20 grams of solid phosgene is added portionwise under stirring,
10 hours are heated to reflux, after reaction, 30 grams of 20% sodium hydroxide is added in, excessive phosgene is quenched, and extracted with toluene,
Dehydration, and toluene layer is concentrated, obtain the 2- amino malononitrile of 9.6g.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (4)
1. a kind of synthetic method of 2- amino malononitrile, which is characterized in that include the following steps：
1）Using diethyl aminomalonate as starting material, the aqueous solution of 40-60w/v% ammonium chlorides is direct plungeed into, in 100-120
At DEG C, 2-5 hour is reacted, is prepared and prepares 2- amino malonamides；
2）By step 1）The 2- amino malonamides being prepared are dissolved in organic solvent, after heat temperature raising, add in solid phosgene, add
Heat reflux 10-12h generation 2- amino malononitrile.
A kind of 2. synthetic method of 2- amino malononitrile according to claim 1, which is characterized in that the aminopropan two
The molar ratio of ammonium chloride is 1 in the aqueous solution of diethyl phthalate and ammonium chloride：2-3.
A kind of 3. synthetic method of 2- amino malononitrile according to claim 1, which is characterized in that the 2- aminopropans
The mass ratio of diamides and solid phosgene is 1:1-1.5.
4. the synthetic method of a kind of 2- amino malononitrile according to claim 1, which is characterized in that the solvent is first
Alcohol, ethyl alcohol or chloroform.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810143901.4A CN108250104A (en) | 2018-02-11 | 2018-02-11 | A kind of synthetic method of 2- amino malononitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810143901.4A CN108250104A (en) | 2018-02-11 | 2018-02-11 | A kind of synthetic method of 2- amino malononitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108250104A true CN108250104A (en) | 2018-07-06 |
Family
ID=62744937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810143901.4A Pending CN108250104A (en) | 2018-02-11 | 2018-02-11 | A kind of synthetic method of 2- amino malononitrile |
Country Status (1)
| Country | Link |
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| CN (1) | CN108250104A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113429310A (en) * | 2021-08-02 | 2021-09-24 | 大连理工大学 | Continuous preparation method of 2-amino malonamide |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100210855A1 (en) * | 2007-09-14 | 2010-08-19 | Kato Nobuo | Sulfonic acid salt compound of 4-carbamoyl-5-hydroxy-imidazole derivative |
| US20100279974A1 (en) * | 2005-03-09 | 2010-11-04 | Claire Pierra | Nucleosides With Non-Natural Bases as Anti-Viral Agents |
| CN105001033A (en) * | 2014-04-16 | 2015-10-28 | 中国石化扬子石油化工有限公司 | Manufacturing method for nitrile and corresponding amine thereof |
| WO2016196910A1 (en) * | 2015-06-05 | 2016-12-08 | Syros Pharmaceuticals, Inc. | Compounds for the modulation of myc activity |
-
2018
- 2018-02-11 CN CN201810143901.4A patent/CN108250104A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100279974A1 (en) * | 2005-03-09 | 2010-11-04 | Claire Pierra | Nucleosides With Non-Natural Bases as Anti-Viral Agents |
| US20100210855A1 (en) * | 2007-09-14 | 2010-08-19 | Kato Nobuo | Sulfonic acid salt compound of 4-carbamoyl-5-hydroxy-imidazole derivative |
| CN105001033A (en) * | 2014-04-16 | 2015-10-28 | 中国石化扬子石油化工有限公司 | Manufacturing method for nitrile and corresponding amine thereof |
| WO2016196910A1 (en) * | 2015-06-05 | 2016-12-08 | Syros Pharmaceuticals, Inc. | Compounds for the modulation of myc activity |
Non-Patent Citations (2)
| Title |
|---|
| 朱彬: "《有机合成》", 31 January 2014, 西南交通大学出版社 * |
| 王欢 等: "法匹拉韦的合成", 《中国医药工业杂志》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113429310A (en) * | 2021-08-02 | 2021-09-24 | 大连理工大学 | Continuous preparation method of 2-amino malonamide |
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Application publication date: 20180706 |
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