Category: 584-13-4

584-13-4,Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4H-1,2,4-Triazol-4-amine, its application will become more common.

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 584-13-4

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 584-13-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 584-13-4, name is 4H-1,2,4-Triazol-4-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 584-13-4. 584-13-4

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4H-1,2,4-Triazol-4-amine.

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 584-13-4 as follows. 584-13-4

5-(4J-l,2,4-Triazol”4-ylamino)-4I-(beiizyIoxy)biphenyl-2-carbonitriIe (CAB06050)To a solution of 4/?-l,2,4-triazol-4-amine (2.439 g, 29.01 mmol) in DMSO (50 mL) was added KOtBu (336 g, 30.0 mmol). The mixture was stirred for 0.5 hours at room temperature before CAB06Theta48 (4.40 g, 14.51 mmol) was added and stirring was continued for 1 hour. The mixture was poured into crashed ice and neutralized with 2M BCHSO4 solution. The precipitate was filtered off and recrystallised from EtOAc/?-hexane to give CAB06050 (5.07 g, 85%) as fine colorless needles. Mp. 180-182 0C; 1H NMR (400 MHz, DMSO-rftf) delta 5.17 (s, 2H)5 6.47 (d, J = 2.4 Hz5 IH), 6.54 (dd, J = 8.6, 2.4 Hz, IH)5 7.15 (AA’BB’, 2H), 732-7.50 (m, 7H)5 7.78 (d, J= 8.6 Hz, IH), 8.86 (s, 2H), 10.28 (S5 IH); 13C NMR (100.6 MHz5 DMSO-rf*) delta 69.4, 101.2, 111.0, 1123, 115.0, 119.1, 127,8, 127.9, 128.5, 129.7, 130.2, 135.6, 136.8, 144.1, 146.0, 150.8, 158.9; LRMS (ES+): m/z 368,2 (100%, [M+H]+); HRMS (ES+) calcd for C22H18N5O [M+H]+: 368.1506, found 368.1494.

According to the analysis of related databases, 584-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics