CN108586379B - Preparation method of 3-aminofurazan-4-formamide - Google Patents

Preparation method of 3-aminofurazan-4-formamide Download PDF

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CN108586379B
CN108586379B CN201810126538.5A CN201810126538A CN108586379B CN 108586379 B CN108586379 B CN 108586379B CN 201810126538 A CN201810126538 A CN 201810126538A CN 108586379 B CN108586379 B CN 108586379B
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aminofurazan
oximidocyanoacetamide
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formamide
cyanoacetamide
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戴立言
李俊
张玲玲
王晓钟
陈英奇
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Zhejiang University ZJU
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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Abstract

The invention discloses a preparation method of 3-aminofurazan-4-formamide, which comprises the following steps: nitrosation and isomerization are carried out on cyanoacetamide to obtain 2-oximidocyanoacetamide, 2-oximidocyanoacetamide reacts with hydroxylamine hydrochloride and organic base to obtain amidoxime intermediate, namely 2-oximido-3-amidoxime acetamide, and 2-oximido-3-amidoxime acetamide carries out ring-closure reaction under the action of thionyl chloride to generate the target product 3-aminofurazan-4-formamide. The method has the advantages of simple process flow, easily obtained raw materials and higher product yield, is suitable for industrial production, and is also a novel synthesis method of the 3-aminofurazan-4-formamide.

Description

Preparation method of 3-aminofurazan-4-formamide
Technical Field
The invention belongs to the technical field of synthesis of organic intermediates, and particularly relates to a preparation method of 3-aminofurazan-4-formamide.
Background
The furazan ring is a five-membered ring containing 2 nitrogen atoms and one oxygen atom, and is also called a 1,2,5-oxadiazole ring (1,2, 5-oxadiazole). The compound is a very effective energetic structural unit due to the characteristics of high enthalpy of formation, good thermal stability, active oxygen in a ring, a large pi conjugated system with aromaticity in a molecule and the like. Researches show that the molecular energy can be greatly increased by the existence of furazan rings in the molecules, and the furazan rings can be released under specific conditions, so that the furazan rings are widely concerned by domestic and foreign scholars.
The 3-aminofurazan-4-formamide is a simple furazan compound, and reacts with different reagents by utilizing the activity of amino and amido on the molecule of the compound, so that a series of furazan derivatives are obtained. The current literature synthesis methods of 3-aminofurazan-4-formamide comprise 3 methods: (1) the preparation method is characterized by taking malononitrile as a raw material, firstly preparing 3-amino-4-amidoximyl furazan (AAOF), then preparing a derivative of AAOF, and further obtaining a target product. The main problems of this method are low product yield, complicated synthesis procedure and poor selectivity (Chemistry of Heterocyclic Compounds (New York, NY, United States),2017,53(6-7), 760-. (2) Methyl cyanoacetate or ethyl cyanoacetate is taken as a raw material, 4-aminofurazan-3-formic acid is prepared firstly, then the raw material reacts with propanol to obtain 4-aminofurazan-3-propyl formate, and finally the target product is obtained through ammonolysis. The main problems of this method are the complicated synthesis steps, the long production cycle of the product, and the low yield of the final product (Organic precursors and products International,2004,36(4), 36362; Journal of Heterocyclic Chemistry,2005,42(4), 519-. (3) Preparing 2-oxyfurazan-3, 4-ethyl diformate by using ethyl acetoacetate as a raw material, then obtaining 2-oxyfurazan-4-aminofurazan-3-formamide, and finally obtaining a target product by deoxyN on a furazan ring. The method has the main problems of complicated synthesis steps, complex post-reaction treatment, long synthesis period and low product yield (Journal of Organic Chemistry,81 (19)), 9415-.
The above three methods are shown by the following formula:
the method comprises the following steps:
Figure BDA0001573659950000021
the method 2 comprises the following steps:
Figure BDA0001573659950000022
the method 3 comprises the following steps:
Figure BDA0001573659950000031
disclosure of Invention
In order to solve the problems of low yield, poor reaction selectivity, complicated synthesis steps and the like of the products, the invention provides a method for preparing 3-aminofurazan-4-formamide by taking cyanoacetamide as a raw material, the method has the advantages of simple and easily obtained raw material, simple and convenient post-treatment and higher yield, solves the problem that the 3-aminofurazan-4-formamide is difficult to prepare from the simple raw material, and is a novel green synthesis method.
The invention takes cyanoacetamide as a raw material to prepare 3-aminofurazan-4-formamide, which comprises the following steps:
the first step is as follows: under the action of acid, cyanoacetamide reacts with sodium nitrite in water, and after the reaction is finished, the reaction solution is filtered to obtain solid, namely 2-oximidocyanoacetamide;
the second step is that: under the action of organic alkali, oximidocyanoacetamide and hydroxylamine hydrochloride react in a condensation solvent, and after the reaction is finished, a solid obtained by filtering reaction liquid is a crude product containing 2-oximido-3-amidoximeacetamide;
the third step: under the action of thionyl chloride, reacting the crude product of the 2-oximido-3-amidoxime acetamide obtained in the second step in a cyclization solvent, and performing post-treatment after the reaction is finished to obtain the 3-aminofurazan-4-formamide.
The method utilizes the property that cyanoacetamide (1) contains active methylene in aqueous solution, sodium nitrite and acid are added for reaction, the methylene on the position can be nitrosated and isomerized into oxime, and 2-oximidocyanoacetamide (2) is prepared; then reacting the obtained 2-oximidocyanoacetamide with hydroxylamine (the hydroxylamine is a product obtained by neutralizing hydroxylamine hydrochloride and organic base) in a condensation solvent to obtain a 2-oximido-3-amidoximeacetamide (3) crude product, and directly using the obtained crude product for the next reaction without purification; and finally, carrying out dehydration ring-closing reaction on the 2-oximido-3-amidoxime acetamide under the action of thionyl chloride to obtain a final product, namely 3-aminofurazan-4-formamide (4).
The above reaction process is shown as the following formula:
Figure BDA0001573659950000041
preferably, the acid used in the first step for preparing 2-oximidocyanoacetamide is hydrochloric acid, sulfuric acid, nitric acid, formic acid or glacial acetic acid. Glacial acetic acid is preferred.
Preferably, the condensation solvent used in the preparation of the amidoxime intermediate 3 in the second step is tetrahydrofuran, anhydrous methanol, anhydrous ethanol, tert-butanol, isopropanol, preferably isopropanol; the organic base is sodium methoxide, sodium ethoxide, potassium tert-butoxide or sodium tert-butoxide, preferably potassium tert-butoxide;
preferably, the cyclization solvent used for preparing the final product 3-aminofurazan-4-formamide in the third step is 1, 4-dioxane, N-methylpyrrolidone, toluene or xylene, and the final product is preferably 1, 4-dioxane;
preferably, in order to further reduce the formation of byproducts and improve the product purity and yield, the temperature in the second step of preparing the amidoxime intermediate 3 is 50-85 ℃, and the temperature in the third step of ring-closing reaction is 60-80 ℃.
Preferably, in order to obtain the target product as much as possible and avoid waste of raw materials, the molar ratio of the sodium nitrite to the cyanoacetamide used in the first step is 1-1.5: 1, H of the acid used+The molar ratio of cyanoacetamide to cyanoacetamide is 1.5-2.5: 1, the weight ratio of water to cyanoacetamide is 5-10: 1; the molar ratio of the hydroxylamine hydrochloride to the organic base used in the second step is 1:1, the molar ratio of the hydroxylamine hydrochloride to the 2-oximidocyanoacetamide is 1-2: 1, and the weight ratio of the condensation solvent to the 2-oximidocyanoacetamide is 5-15: 1; the molar ratio of the thionyl chloride to the 2-oximidocyanoacetamide used in the third step is 1-2: 1; the weight ratio of the cyclization solvent to the 2-oximidocyanoacetamide is 5-15: 1.
Preferably, the post-treatment of the third step is: and (3) concentrating the reaction solution, then adding water for dilution, extracting with ethyl acetate, layering, drying a product layer, concentrating, and refining to obtain the target product 3-aminofurazan-4-formamide.
Compared with the prior art, the invention has the following advantages:
the method has the advantages of simple process flow, easily obtained raw materials, simple post-treatment and higher purity and yield of the final product, can be used for industrial production, is a novel green synthesis method of the 3-aminofurazan-4-formamide, solves the problems of difficulty, low yield and the like in the preparation of the 3-aminofurazan-4-formamide in the traditional process, and provides a new synthesis route for synthesizing amide to replace furazan.
Drawings
FIG. 1 is a nuclear magnetic spectrum diagram of the first step product 2-oximidocyanoacetamide 2, the nuclear magnetic data are as follows:1H NMR(500MHz,DMSO-d6):7.83,7.91(2br s,2H,CONH 2),14.48(s,1H,OH)；
FIG. 2 is a nuclear magnetic hydrogen spectrum of the second step product 2-hydroxyimino-3-amidoxime acetamide 3, with nuclear magnetic data as follows:1HNMR(500MHz,DMSO-d6):5.86(s,2H,NH 2),7.31,7.52(2br s,2H,CONH 2),9.80(s,1H,OH),12.72(s,1H,OH)；
FIG. 3 is a nuclear magnetic hydrogen spectrum diagram of the product 3-aminofurazan-4-formamide 4 in the third step, and nuclear magnetic data are as follows:1HNMR(500MHz,DMSO-d6):6.34(s,2H,NH 2),8.06,8.43(2br s,2H,CONH 2)。
Detailed Description
Example 1
The first step is as follows: synthesis of 2-oximidocyanoacetamide (2)
Figure BDA0001573659950000061
100m L of deionized water is added into a 250m L reaction bottle, cyanoacetamide 1(12.61g, 0.15mol) and sodium nitrite (12.42g, 0.18mol) are weighed and sequentially added into the reaction bottle, glacial acetic acid (17.1m L, 0.3mol) is added dropwise under the condition of ice-water bath, stirring is carried out for 10 hours at room temperature after dropwise addition is finished, T L C tracks the reaction progress, after the reaction is finished, a white filter cake is obtained by suction filtration and is placed into an oven to be dried to obtain white powder (14.48g, the molar yield is 85.4%).
The melting point is 171.8-172.0 DEG C
1H NMR(500MHz,DMSO-d6):7.83,7.91(2br s,2H,CONH 2),14.48(s,1H,OH)。
The second step and the third step are synthesized by a one-pot method: synthesis of 3-aminofurazan-4-carboxamide (4)
Figure BDA0001573659950000062
Adding 3.6m L anhydrous methanol into a dry reaction bottle, weighing 27.5% by mass of a methanol solution of sodium methoxide (1.47g, 7.5mmol) and hydroxylamine hydrochloride (0.52g, 7.5mmol) and sequentially adding into the reaction bottle, stirring for 0.5h, then adding 2(0.57g, 5mmol), stirring for 6h at 70 ℃, after the reaction is finished, filtering the reaction liquid to obtain a solid which is a crude product containing 2-oximido-3-amidoxime acetamide 3, directly dissolving the dried crude product with 1, 4-dioxane (2.7m L), then dropwise adding thionyl chloride (0.89g, 7.5mmol), stirring and reacting for 4h at 60 ℃, tracking process T L C, carrying out suction filtration, after the reaction is finished, washing a filter cake to white with a little 1, 4-dioxane, concentrating the obtained filtrate, adding water for dilution, and extracting with ethyl acetate, and refining to obtain a target product layer (yield of 4.36 g, 2 mol%).
Example 2
The first step is as follows: synthesis of 2-oximidocyanoacetamide (2)
Adding 63m L of deionized water into a 250m L reaction bottle, then weighing cyanoacetamide 1(12.61g, 0.15mol) and sodium nitrite (11.38g, 0.16mol) to be sequentially added into the reaction bottle, dropwise adding formic acid (8.5m L, 0.22mol) under the condition of ice-water bath, stirring for 8h at room temperature after dropwise adding, tracking the reaction process by T L C, after the reaction is finished, performing suction filtration to obtain a white filter cake, and placing the white filter cake in an oven to be dried to obtain white powder (14.07g, the molar yield is 83.0%).
The second step and the third step are synthesized by a one-pot method: synthesis of 3-aminofurazan-4-carboxamide (4)
Adding 4.6m L anhydrous methanol into a dried reaction bottle, weighing 21% by mass of an ethanol solution (3.20g, 10mmol) of sodium ethoxide and 0.70g, 10mmol of hydroxylamine hydrochloride, sequentially putting the ethanol solution and the hydroxylamine hydrochloride into the reaction bottle, stirring for 0.5h, then adding 2(0.57g, 5mmol), stirring for 8h at 50 ℃, after the reaction is finished, filtering the reaction solution to obtain a solid which is a crude product containing 2-oximido-3-amidoxime acetamide 3, directly dissolving the dried crude product with N-methylpyrrolidone (5.5m L), then dropwise adding 1.19g, 10mmol of thionyl chloride, stirring and reacting for 2h at 80 ℃, tracking the reaction at T L C, performing suction filtration, washing a filter cake with a little N-methylpyrrolidone to white, concentrating the obtained filtrate, adding water for dilution, extracting with ethyl acetate, concentrating the product layer, and refining to obtain the target product 4(0.34g, molar yield of 53.1%).
Example 3
The first step is as follows: synthesis of 2-oximidocyanoacetamide (2)
Adding 113m L of deionized water into a 250m L reaction bottle, then weighing cyanoacetamide 1(12.61g, 0.15mol) and sodium nitrite (10.35g, 0.15mol) to be sequentially added into the reaction bottle, dripping 75% by mass of sulfuric acid (11.9m L, 0.15mol) under the condition of ice-water bath, stirring for 12h at room temperature after dripping is finished, tracking the reaction progress by T L C, performing suction filtration to obtain a white filter cake, and placing the white filter cake in an oven to be dried to obtain white powder (13.92g, 82.1% of molar yield).
The second step and the third step are synthesized by a one-pot method: synthesis of 3-aminofurazan-4-carboxamide (4)
Adding 11m L anhydrous tert-butyl alcohol into a dry reaction bottle, weighing sodium tert-butoxide (0.48g, 5mmol) and hydroxylamine hydrochloride (0.35g, 5mmol), sequentially adding into the reaction bottle, stirring for 0.5h, then adding 2(0.57g, 5mmol), stirring for 5h at 85 ℃, after the reaction is finished, filtering the reaction solution to obtain a solid which is a crude product containing 2-oximido-3-amidoxime acetamide 3, directly dissolving the dried crude product with toluene (9.8m L), then dropwise adding thionyl chloride (0.60g, 5mmol), stirring and reacting for 3h at 70 ℃ after dropwise adding, tracking the process T L C, after the reaction is finished, performing suction filtration, washing a filter cake with a little toluene to be white, concentrating the obtained filtrate, adding water for dilution, extracting with ethyl acetate, concentrating the product layer, and refining to obtain a target product 4(0.30g, and the molar yield of 46.9%).
Example 4
The first step is as follows: synthesis of 2-oximidocyanoacetamide (2)
Adding 126m L of deionized water into a 250m L reaction bottle, then weighing cyanoacetamide 1(12.61g, 0.15mol) and sodium nitrite (13.46g, 0.20mol) to be sequentially added into the reaction bottle, dripping nitric acid (24.0m L, 0.38mol) with the mass fraction of 69.2% under the condition of ice-water bath, stirring for 11h at room temperature after dripping is finished, tracking the reaction progress by T L C, performing suction filtration to obtain a white filter cake, and placing the white filter cake in an oven to be dried to obtain white powder (14.37g, 84.8% of molar yield).
The second step and the third step are synthesized by a one-pot method: synthesis of 3-aminofurazan-4-carboxamide (4)
Adding 5m L anhydrous tetrahydrofuran into a dry reaction bottle, weighing potassium tert-butoxide (0.95g, 8.5mmol) and hydroxylamine hydrochloride (0.59g, 8.5mmol), sequentially adding into the reaction bottle, stirring for 0.5h, then adding 2(0.57g, 5mmol), stirring for 7h at 75 ℃, after the reaction is finished, filtering the reaction solution to obtain a solid which is a crude product containing 2-hydroxyimino-3-amidoxime acetamide 3, directly dissolving the dried crude product with xylene (8.0m L), then dropwise adding thionyl chloride (1.01g, 8.5mmol), stirring for reacting for 3h at 75 ℃, tracking the reaction by T L C, performing suction filtration, washing a filter cake to be white with a little xylene, concentrating the obtained filtrate, adding water for dilution, extracting with ethyl acetate, concentrating the product layer, and refining to obtain the target product 4(0.34g, molar yield 53.1%).
Example 5
The first step is as follows: synthesis of 2-oximidocyanoacetamide (2)
Adding 90m L of deionized water into a 250m L reaction bottle, then weighing cyanoacetamide 1(12.61g, 0.15mol) and sodium nitrite (15.52g, 0.22mol) to be sequentially added into the reaction bottle, dripping 37% hydrochloric acid (22.6m L, 0.27mol) under the condition of ice-water bath, stirring for 9h at room temperature, tracking the reaction progress by T L C, filtering to obtain a white filter cake, and placing the white filter cake in an oven to be dried to obtain white powder (14.30g, 84.4% of molar yield).
The second step and the third step are synthesized by a one-pot method: synthesis of 3-aminofurazan-4-carboxamide (4)
Adding 9m L anhydrous isopropanol into a dry reaction bottle, weighing sodium tert-butoxide (0.58g, 6mmol) and hydroxylamine hydrochloride (0.42g, 6mmol) and sequentially adding into the reaction bottle, stirring for 0.5h, then adding 2(0.57g, 5mmol), stirring for 6h at 60 ℃, after the reaction is finished, filtering the reaction solution to obtain a solid which is a crude product containing 2-oximido-3-amidoxime acetamide 3, directly dissolving the dried crude product with 1, 4-dioxane (5.0m L), then dropwise adding thionyl chloride (0.71g, 6mmol), stirring for reaction for 4h at 65 ℃, tracking the process T L C, after the reaction is finished, performing suction filtration, washing the filter cake with 1, 4-dioxane to white, concentrating the obtained filtrate, adding water for dilution, extracting with ethyl acetate, concentrating the product layer, and refining to obtain the target product 4(0.38g, the molar yield of 59.4%).
Comparison of the target products obtained in examples 1 to 5 with the pure 3-aminofurazan-4-carboxamide 4, T L C has the same RfThe values, nuclear magnetic data and melting point data are consistent with the existing literature.
Melting point: 176.2 deg.C-176.4 deg.C
1HNMR(500MHz,DMSO-d6):6.34(s,2H,NH 2),8.06,8.43(2br s,2H,CONH 2).
Meanwhile, 2-oximido-3-amidoxime acetamide 3 is separated, and the nuclear magnetic data are as follows:
1H NMR(500MHz,DMSO-d6):5.86(s,2H,NH2),7.31,7.52(2br s,2H,CONH 2),9.80(s,1H,OH),12.72(s,1H,OH).

Claims (5)

1. a preparation method of 3-aminofurazan-4-formamide is characterized by comprising the following steps:
the first step is as follows: under the action of acid, cyanoacetamide reacts with sodium nitrite in water, and after the reaction is finished, the reaction solution is filtered to obtain solid, namely 2-oximidocyanoacetamide;
the second step is that: under the action of organic alkali, oximidocyanoacetamide and hydroxylamine hydrochloride react in a condensation solvent, and after the reaction is finished, a solid obtained by filtering reaction liquid is a crude product containing 2-oximido-3-amidoximeacetamide;
the condensation solvent is tetrahydrofuran, anhydrous methanol, anhydrous ethanol, tert-butanol or isopropanol
The third step: under the action of thionyl chloride, reacting the crude product of the 2-oximido-3-amidoxime acetamide obtained in the second step in a cyclization solvent, and performing post-treatment after the reaction is finished to obtain the 3-aminofurazan-4-formamide;
the cyclization solvent used in the third step is 1, 4-dioxane, N-methyl pyrrolidone, toluene or xylene.
2. The process for producing 3-aminofurazan-4-carboxamide according to claim 1, characterized in that the acid used in the first step is hydrochloric acid, sulfuric acid, nitric acid, formic acid or glacial acetic acid;
the organic base used in the second step is: sodium methoxide, sodium ethoxide, potassium tert-butoxide or sodium tert-butoxide.
3. The preparation method of 3-aminofurazan-4-formamide according to claim 1, wherein the molar ratio of sodium nitrite to cyanoacetamide used in the first step is 1-1.5: 1, H of the acid used+The molar ratio of cyanoacetamide to cyanoacetamide is 1.5-2.5: 1, the weight ratio of water to cyanoacetamide is 5-10: 1;
the molar ratio of the hydroxylamine hydrochloride to the organic base used in the second step is 1:1, the molar ratio of the hydroxylamine hydrochloride to the 2-oximidocyanoacetamide is 1-2: 1, and the weight ratio of the condensation solvent to the 2-oximidocyanoacetamide is 5-15: 1;
the molar ratio of the thionyl chloride to the 2-oximidocyanoacetamide used in the third step is 1-2: 1; the weight ratio of the cyclization solvent to the 2-oximidocyanoacetamide is 5-15: 1.
4. The preparation method of 3-aminofurazan-4-carboxamide according to claim 1, characterized by the following specific steps:
the first step is as follows: dissolving cyanoacetamide and sodium nitrite in water, dropwise adding acid under the condition of ice-water bath, stirring at room temperature for 8-12 h after dropwise adding, and filtering the reaction liquid to obtain a solid, namely 2-oximidocyanoacetamide;
the second step is that: dissolving hydroxylamine hydrochloride and organic alkali in a condensation solvent, stirring for half an hour, adding the 2-oximidocyanoacetamide obtained in the first step into a reaction solution, reacting for 5-8 hours at 50-85 ℃, and filtering the reaction solution to obtain a solid which is a crude product containing 2-oximido-3-amidoximetamide;
the third step: and (3) completely dissolving the crude product of the 2-oximido-3-amidoxime acetamide obtained in the second step in a cyclization solvent, adding thionyl chloride at the temperature of 60-80 ℃ for reacting for 2-4 h, and carrying out aftertreatment to obtain the target product 3-aminofurazan-4-formamide.
5. The process for producing 3-aminofurazan-4-carboxamide according to claim 4, characterized in that the post-treatment of the third step is: and (3) concentrating the reaction solution, then adding water for dilution, extracting with ethyl acetate, layering, drying a product layer, concentrating, and refining to obtain the target product 3-aminofurazan-4-formamide.
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