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New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 4928-88-5

EXAMPLE 9 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for hours, while maintaining the temperature of the reaction mixture at 95+-5° C. And then, the reaction mixture was crystallized with 421.1 ml of methanol to give 64 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 88percent).

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Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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EXAMPLE 1 1-(d,l-Tetrahydropyran-2-yl)-1,2,4-triazole-3-carboxamide A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g, 0.10 mole), 2,3-dihydropyran (16 ml), bis(p-nitrophenyl) phosphate (0.10 g) and anhydrous dimethylformamide (100 ml) was heated at 75°-80° for 3 hrs. Additional 2,3-dihydropyran (8 ml) was added and heating at 75°-80° was continued for 3 hrs. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (150 ml). The ethyl acetate solution was washed with aqueous sodium hydrogen carbonate (two 25 ml portions) and water. The solution was dried over magnesium sulfate, filtered and the filtrate was evaporated to dryness. The crude product, methyl 1-(d,l-tetrahydropyran-2-yl)-1,2,4-triazole-3-carboxylate, was treated for 20 hrs at 25° with methanol saturated with anhydrous ammonia. The solvent was removed in vacuo and the product was crystallized from ethanol to provide 14.0 g (71percent). Recrystallization from ethanol afforded 11.7 g (60percent) of pure 1-(d,l-tetrahydropyran-2 -yl)-1,2,4-triazole-3-carboxamide with mp 156°-158°. NMR (DMSO-d6) delta 8.82 (S, 1, H-5). Anal. Calcd for C8 H12 N4 O2: C, 48.97; H, 6.17; N, 28.56. Found: C, 48.95; H, 6.22; N, 28.42.

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Reference:
Patent; ICN Pharmaceuticals, Inc.; US3991078; (1976); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Synthetic Route of 4928-88-5, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Example 3A Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (20) A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-beta-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165° C.). The flask was connected to a water aspirator and kept at 160-165° C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3 –>EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66percent) of pure product: 1 H NMR (CDCl3) delta 2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 4.22 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′,), and 8.38 (s, 1H, C3 H). Anal. Calc. for C15 H19 N3 O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

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Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Application of 4928-88-5, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 250 mL four-necked flask equipped with a mechanical stirrer, thermometer and distillation apparatus, 100.0 g of tetraacetyl ribose was added and heated to 100 ° C in an oil bath.After the tetraacetyl ribose is completely melted into a transparent liquid, the stirring is started.40.0 g of methyl 1,2,4-triazolecarboxylate was added, and the two materials were uniformly mixed.Add 1.4g of elemental iodine, continue to raise the temperature to 115 ° C, and keep warm for 2 hours.Then, vacuuming was started, and by-product acetic acid was distilled off; after 1 hour, the reaction was stopped, and the mixture was cooled to 70 ° C or lower, 100 mL of methanol was taken, and the mixture was added to the flask, and the mixture was stirred to uniformly dissolve the material, and poured into a beaker. Allow to cool to room temperature,Precipitate solids, filter, wash, dry,Ribavirin intermediate[1-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester], yield 82percent (Based on tetraacetyl ribose, the same below.)

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Reference:
Patent; Henan Academy Of Sciences High Technology Research Center; Zhang Jiaxiang; Guo Xiaozhan; Chen Tiantian; Wang Huafen; Ren Zhiyong; Gong Wei; Fu Yang; Jiang Lei; (10 pag.)CN109336937; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Research speed reading in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 1H-1,2,4-triazole-3-carboxylate

EXAMPLE 3 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 105+-5° C. And then, the reaction mixture was crystallized with 300.8 ml of methanol to give 58.6 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 80percent).

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Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Synthetic Route of 4928-88-5, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

EXAMPLE 8 A mixture of methyl 1,2,4-triazole-3-carboxylate (26.4 g, 0.21 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (60.2 g, 0.19 mole) was melted and then 1.1 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 5 hours, while maintaining the temperature of the reaction mixture at 95+-5° C. And then, the reaction mixture was crystallized with 180.5 ml of methanol to give 68.9 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 95percent).

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Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about Methyl 1H-1,2,4-triazole-3-carboxylate is helpful to your research.

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EXAMPLE 15 A mixture of methyl 1,2,4-triazole-3-carboxylate (1.27 g, 0.01 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (3.18 g, 0.01 mole) was melted and then 0.076 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 95+-5° C. And then, the reaction mixture was crystallized with 20 ml of butanol to give 2.70 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 85percent).

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about Methyl 1H-1,2,4-triazole-3-carboxylate is helpful to your research.

Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Reference of 4928-88-5, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

EXAMPLE 16 A mixture of methyl 1,2,4-triazole-3-carboxylate (1.27 g, 0.01 mole) and beta-D-ribofuranosyl-1,2,3,5-tetraacetate (3.18 g, 0.01 mole) was melted and then 0.076 g of p-toluenesulfonic acid was added thereto. The reaction mixture was reacted for 3 hours, while maintaining the temperature of the reaction mixture at 95+-5° C. And then, the reaction mixture was crystallized with 20 ml of isobutanol to give 2.92 g of 1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester (yield: 92percent).

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Reference:
Patent; Lee, Tai-Au; Park, Nam-Jin; Khoo, Ja-Heouk; Lee, Byung-Cheol; US2003/120064; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Application of 4928-88-5, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

EXAMPLE 5 Preparation of Methyl 1-(2,3,5-tri-O-Acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate From Alpha-1,2,3,5-tetra-O-acetyl-L-ribofuranose [0047] A 250 mL flask was charged with [0048] 1.92 g of triazolemethylester and a solution of [0049] 4.8 g of the pure alpha-1,2,3,5-tetra-O-acetyl-L-ribofuranose, prepared in Example 4 in [0050] 50 mL of methyl acetate. The mixture was concentrated at atmospheric pressure to almost dryness (bath temperature: 90° C.). To this mixture was added a solution of [0051] 22.7 mg of triflic acid in 1 mL of methyl acetate. The mixture was stirred at 115+/-5° C. (pot temperature) under vacuum (30 mbar) for 4 h. Upon the completion of the reaction the mixture was cooled to 70° C. and to it was added [0052] 23 mL of 2B alcohol (ethyl alcohol). When a homogeneous solution was formed the mixture was cooled to 50° C. and held until heavy precipitation formed. The mixture was then slowly cooled to -5° C. (bath temperature) in 2 h and held for 13 h. The solid was filtered, washed with [0053] 20 mL of cold 2B Alcohol (ethyl alcohol), and dried under vacuum at 50° C. for 17 h to give 4.1 g (70percent yield) of methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate as an off-white solid.

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Reference:
Patent; Dong, Zhiming; Zhang, Pingsheng; US2004/34213; (2004); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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Application of 4928-88-5, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 4928-88-5, name is Methyl 1H-1,2,4-triazole-3-carboxylate, molecular formula is C4H5N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

In a 6000 ml 4-necked anhydrous reactor equipped with a thermometer, a condenser and a mechanical stirrer, 1680 ml of dichloromethane, 400.05 g of tetraacetyl ribose and 185.11 g of 3-carbomethoxytriazole were added while stirring and introducing nitrogen. The mixture was cooled to about 5 ° C and 360.03 g of tin tetrachloride was added to the suspension as a trickle while stirring, and the reaction was allowed to exotherm by cooling with an ice bath so that the temperature did not exceed 15-20 °C, and when fully added, the reaction mixture was heated to reflux for 2 h, cooled to 20 ° C with water and ice bath over 15 min.Then 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml) were added at a temperature below +20 ° C and stirred for 45 min; the mixture was allowed to stand for 15 min to separate, and then the aqueous phase of the upper layer was separated from the enriched organic phase, followed by The organic phase was treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml).After stirring for 45 min, the mixture was allowed to stand for 15 min to separate the phases, the upper aqueous phase was separated from the enriched organic phase, and then the organic phase was treated with 30percent hydrochloric acid (176.7 ml) and water (1503.3 ml). After 45 minutes,The mixture was allowed to stand for 15 min to separate the phases by phase separation: the organic phase was distilled at atmospheric pressure (internal temperature 45 ° C) and 3000 ml of toluene was added to the oil residue, and the mixture was distilled under vacuum at a residual pressure of about 200 mbar. Stirred moist paste.It was allowed to cool to 5-10 ° C for 2 h and was filtered on a Buchner funnel while washing with toluene. 521.36 g of a moist product were obtained.

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Reference:
Patent; Li Shuangxi; (12 pag.)CN109134565; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics