cas 1455-77-2, 1H-1,2,4-Triazole-3,5-diamine

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Efficient in situ synthesis of 3,5-disubstituted-1,2,4-triazoles under microwave-assisted conditions
Abstract Based on an efficient in situ metal/ligand reaction, a serial of 3,5-disubstituted-1, 2,4-triazoles were synthesized via cycloaddition of organonitriles and ammonia under microwave conditions. This synthetic protocol provides a concise and high-yield access to 3,5-disubstituted-1,2,4-triazoles in organic synthesis. Moreover, the tautomerism of the product was also investigated. Taylor & Francis Group, LLC.
Wei, Qing,Qiao, Chengfang,Xia, Zhengqiang,Chen, Sanping
p. 3181 - 3191
(2013)
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Preparation and characterization of 3,5-dinitro-1H-1,2,4-triazole
Neat 3,5-dinitro-1H-1,2,4-triazole was obtained in quantitative yield from potassium 3,5-dinitro-1,2,4-triazolate and sulfuric acid. The compound was purified by sublimation in vacuo at 110 °C. Pure HDNT is a hygroscopic white solid that is impact and friction sensitive and decomposes explosively upon heating to 170 °C. However, the presence of impurities might lower the decomposition temperature and increase the sensitivity of the material. Potassium 3,5-dinitro-1,2,4-triazolate was prepared from commercially available 3,5-diamino-4H-1,2,4-triazole with sodium nitrite and sulfuric acid. The synthesis of HDNT from 2-cyanoguanidine and hydrazine hydrate without isolation and purification of the 3,5-diamino-4H-1,2,4-triazole intermediate can result in the formation of azidotriazole impurities. A triclinic and a monoclinic polymorph of 3,5-dinitro-1H-1,2,4-triazole were found by X-ray structure determination. In addition, the crystal structure of the hydrate (HDNT)3·4H2O, as well as those of several HDNT impurities and decomposition products were obtained.
Haiges,Bélanger-Chabot,Kaplan,Christe
p. 7586 - 7594
(2015)
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Technology for three-innovation synthesis of 2-amino-5-methyl-4-oxo-3-n-propyltriazolopyrimidine
The invention discloses a technology for synthesizing 2-amino-5-methyl-4-oxo-3-n-propyl-6H-triazolo-[1,5-a]pyrimidine. Methyl methacrylate and bromine are firstly subjected to an addition reaction toprepare methyl 2,3-dibromo-2-methylpropanoate, and then the methyl 2,3-dibromo-2-methylpropanoate and sodium methylate are etherified in a new suitable solvent to prepare methyl 3,3-dimethoxy-2-methylpropionate etherate; the etherate and 3,5-diamino-1,2,4-triazole, prepared from hydrazine hydrate and dicyandiamide under the catalysis of an acid, are condensed at an intermediate temperature of about 115 DEG C under the catalysis of an organic base to obtain a pyrimidotriazole compound; and the pyrimidotriazole material liquid and 1-chloropropane undergo a direct alkylation reaction in an inorganic or organic bas and a new solvent to obtain the 2-amino-5-methyl-4-oxo-3-n-propyl-6H-triazolo-[1,5-a]pyrimidine. The technology is improved by the three major innovations of improving the catalyticsynthesis conditions of the condensation ring closure of the pyrimidotriazole, optimizing the alkylation substitution reaction and the process technology of the pyrimidinetriazole and innovating theraw material of an alkylation reagent, so the technology has the advantages of great improvement of the yield, simplicity in operation, mild reaction conditions, and safety to devices and human bodies, the total yield of methyl methacrylate can reach 46.5% or above, and the obtained product has a white color and a good crystalline state, and has a content of 99% or more.
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Paragraph 0015; 0029

(2019/11/29)

Silica Metal Oxide Vesicles Catalyze Comprehensive Prebiotic Chemistry
It has recently been demonstrated that mineral self-assembled structures catalyzing prebiotic chemical reactions may form in natural waters derived from serpentinization, a geological process widespread in the early stages of Earth-like planets. We have s
Mattia Bizzarri, Bruno,Botta, Lorenzo,Pérez-Valverde, Maritza Iveth,Saladino, Raffaele,Di Mauro, Ernesto,García-Ruiz, Juan Manuel
p. 8126 - 8132
(2018/05/29)

Hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole
The invention provides a hydrothermal synthesis method of 3,5-diamino-1,2,4-triazole. The method comprises the following steps: cyan substituted derivatives, ammonium salt, copper hydroxide and water are used as raw materials, hydrothermal synthesis is carried out in a condition with high pressure, and 3,5-diamino-1,2,4-triazole is obtained. Cyanamide, ammonium salt, and copper hydroxide are used as raw materials, a high pressure reaction apparatus is used, ammonia which is decomposed from the ammonium salt in the effects of copper hydroxide and two molecules of cyanamide are condensed, in order to generate a copper biguanide complex. Copper(I) sulfide is eliminated from the copper biguanide complex in a condition with existence of sulfide, and 3,5-diamino-triazole is obtained by a cyclocondensation reaction. A high pressure reaction vessel is used for increasing the concentration of ammonia in a water system, which is good for generation of the condensation reaction, and at the same time, time and temperature required for condensation of cyanamide are effectively reduced. Existence of excess ammonium salt is used, in order to stabilize the pH value of the whole reaction system, and generation of the side reaction of polymerization of cyanamide is avoided. The method has the advantages of simple process, low raw material cost, and high purity of the final product.
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Paragraph 0073; 0074; 0075

(2018/02/04)

Synthesis and structural characterization of N-amino compounds
Seven N-amino compounds were successfully synthesized via N-amination reaction. The structures of target compounds and intermediates were characterized by 1H NMR, 13C NMR, IR, elementary analysis, MS and X-ray single-crystal diffraction analysis. The single crystals of 3,5-diamino-1,2,4-triazole and 3,5-dinitro-1,2,4-triazole were obtained. Crystal data of 3,5-diamino-1,2,4-triazole: C2H5N5, Mr = 99.11, Monoclinic, P2(1)/c, a = 10.652(4), b = 4.3411(14), c = 10.822(4) ?, α = 90(4), β = 118.714(4), γ = 90deg;, V = 0.4389(2) nm3, Z = 4, Dc = 1.500 g cm-3, μ = 0.113 mm-1, F(000) = 208, R = 0.0354 and wR = 0.0936. Crystal data of 3,5-dinitro-1,2,4-triazole: C2H3N5O5, Mr = 177.09, Orthorhombic, P2(1)2(1)2(1), a = 4.937(3), b = 9.344(5), c = 140447(7) ?, α = 90, β = 90, γ = 90°, V = 0.6665(6) nm3, Z = 4, Dc = 1.765 g cm-3, μ = 0.171 mm-1, F(000) = 360, R = 0.0555 and wR = 0.1772.
Li, Ya-Nan,Liu, Ning,Su, Peng-Fei,Wang, Ying-Lei,Ge, Zhong-Xue,Li, Hui,Wang, Bo-Zhou
p. 7151 - 7156
(2015/04/22)

Ionic liquids based on azolate anions
Compartmentalized molecular level design of new energetic materials based on energetic azolate anions allows for the examination of the effects of both cation and anion on the physiochemical properties of ionic liquids. Thirty one novel salts were synthesized by pairing diverse cations (tetraphenylphosphonium, ethyltriphenylphosphonium, /V-phenyl pyridinium, 1butyl-3-methylimidazolium, tetramethyl-, tetraethyl-, and tetrabutylammonium) with azolate anions (5-nitrobenzimidazolate, 5-nitrobenzotriazolate, 3,5-dinitro-1,2,4-triazolate, 2,4-dinitroimidazolate, 4-nitro-l ,2,3-triazolate, 4,5-dinitroimidazolate, 4,5-dicyanoimidazolate, 4-nitroimidazolate, and tetrazolate). These salts have been characterized by DSC, TGA, and single crystal X-ray crystallography. The azolates in general are surprisingly stable in the systems explored. Ionic liquids were obtained with all combinations of the l-butyl-3-methylimidazoli-um cation and the heterocyclic azolate anions studied, and with several combinations of tetraethyl- or tetrabutylammonium cations and the azolate anions. Favorable structure-property relationships were most often achieved when changing from 4- and 4,5-disubstituted anions to 3,5- and 2,4-disubstituted anions. The most promising anion for use in energetic ionic liquids of those studied here, was 3,5-dinitro-l ,2,4-triazolate, based on its contributions to the entire set of target properties.
Smiglak, Marcin,Corey Hines,Singh, Shailendra,Wilsion, Timothy B.,Vincek, Adam S.,Kirichenko, Kostyantyn,Katritzky, Alan R.,Rogers, Robin D.
experimental part
p. 1572 - 1584
(2010/06/11)

Regioselective synthesis of alkyl derivatives of 3,5-diamino-1,2,4-triazole
New procedures were suggested for regioselective synthesis of alkyl derivatives of 3,5-diamino-1,2,4-triazole. Pleiades Publishing, Inc., 2006.
Chernyshev,Rakitov,Astakhov,Sokolov,Zemlyakov,Taranushich
p. 624 - 630
(2008/02/05)

Process for the synthesis and recovery of nitramines
A method is provided for the synthesis of nitramines, and the recovery of the nitramines from a clathrate.
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(2008/06/13)

Composition of matter having bioactive properties
Particles of coordinated complex comprising a basic, hydrous polymer and a capacitance adding compound, as well as methods for their production, are described. These complexes exhibit a high degree of bioactivity making them suitable for a broad range of applications through their incorporation into conventional vehicles benefiting from antimicrobial and similar properties.
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(2008/06/13)

Formation of 3,5-diamino-1,2,4-triazole and 3,5,7-triamino-1,2,4-triazolo[4,3-a]-1,3,5-triazine in melts of dicyanodiamide and hydrazine salts
Formation of 3,5-diamino-1,2,4-triazoIe and 3,5,7-triamino-1,2,4-triazolo[4,3a]-1,3,5-triazine was studied in relation to the reactant ratio and reaction temperature.
Chernyshev,Zemlyakov,Taranushich
p. 1780 - 1783
(2007/10/03)

On Triazoles. XXVIII. Synthesis of Isomeric 1,2,4-Triazolylcarbothiohydrazides
Different 3a, 3b, 9, 10 and 12 type 5-amino-1,2,4-triazolylcarbothiohydrazide isomers representing all possible isomeric types derived from 5-amino-1,2,4-triazoles were synthesised from the corresponding 5-amino-1,2,4-triazolyldithiocarbonates and hydrazines.HPLC measurements proved that in case of monosubstituted hydrazines the steric press in the intermediate 6 caused besides formation of the expected derivative 3a the formation of compounds 4 and 5, too, while the intermediate 7 yielded only 3b.Thermal rearangement of derivatives 3a in acetic acid led to isomers 9 and 10, respectively.
Barkoczy, Jozsef,Reiter, Jozsef
p. 1677 - 1683
(2007/10/02)

Ethylenic silicon compounds and thermoplastic elastomers obtained therefrom
The invention provides organosilicon compounds of the formula: STR1 in which: N IS 1, 2 OR 3; Each R, which may be identical or different, is a monovalent organic group which contains a carbon-carbon double bond and from 2 to 10 carbon atoms; Each R1, which may be identical or different, is a straight or branched alkyl radical optionally substituted by one or more halogen atoms or cyano groups; an aryl radical or an alkylaryl radical optionally substituted by one or more halogen atoms; R2 is a straight or branched divalent alkylene or alkylidene radical possessing up to 4 carbon atoms; X is a divalent radical consisting of, or containing, at least one hetero-atom selected from oxygen, sulphur and nitrogen atoms, the radical being attached to the radical R2 via a said hetero-atom; G is an organic radical of valency (m+ l) possess from 1 to 30 carbon atoms; m is 1, 2 or 3; And each Y, which may be identical or different, is a functional group selected from: --NO2, STR2 --COOM (where M represents a sodium, potassium or lithium atom); --COOR4 ; STR3 --COCl; --OH; --OR4 ; STR4 --SH; --SR4 ; STR5 --CONH2 ; --CSNH2 ; --CN; --CH2 --NH2 ; --CHO; STR6 --NCO; STR7 wherein R3 represents a hydrogen atom or a straight or branched alkyl radical possessing up to 6 carbon atoms and R4 represents an alkyl radical possessing up to 4 carbon atoms, with the proviso that two Y groups can together constitute an imide group STR8 wherein R5 represents a hydrogen atom or a straight or branched alkyl radical possessing up to 4 carbon atoms. These are useful intermediates in the preparation of disilanes and silicon polymers, in particular of polyethylenic silicon compounds which can be polymerized with an α, ω-dihydrogenopolysiloxane to give thermoplastic elastomers.
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(2008/06/13)