Category: 16681-65-5

Application of 16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, its 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.

Intermediate 53: step a (1-methyl-1H-1,2,3-triazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methanol A 50 mL flask containing 1 -methyl- lH-l ,2,3-triazoie (0.47 g, 5.71 mmol) in dry THF (3 mL) was cooled to -43 C (CH3CN-CO2 bath). -Butyllithium (2.5 M in THF, 2.43 mL, 6.08 mmol) was then added dropwise resulting in a light blue suspension. The suspension was stirred at -40 C for 40 minutes, and then a homogeneous solution of 6-(trifluoromethyl)nicotinaldehyde (1 g, 5.71 nimol) in THF (7 niL) was introduced at -40 C, The resulting homogeneous colorless solution was allowed to warm gradually to room temperature, and after 30 minutes, LC/MS showed that the reaction was complete. The mixture was quenched with water and aqueous NH4CI and extracted with EtOAc (2 x). The combined organic extracts were washed with brine, dried over Na2S04, filtered and concentrated to provide the title compound as a semi-solid which was carried on to the next step without, further purification.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 16681-65-5

A solution of n-butyllithium in hexanes (2.5 M, 22.5 mL, 56.3 mmol) was added dropwise by syringe to a stirring solution of 1-methyl-1H-1,2,3-triazole (5.00 g, 60.2 mmol, prepared according to PCT Int. Appl., 2008098104) in dry tetrahydrofuran (400 mL) at -55 C. The resulting off-white slurry was stirred at -45 C. for 20 minutes, whereupon a solution of 2,6-dimethyl-pyridine-3-carbaldehyde (8.33 g, 61.7 mmol) in dry tetrahydrofuran (10 mL) was added dropwise by syringe. After 5 minutes, the cooling bath was removed and the reaction mixture was allowed to slowly warm. After 45 minutes, saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (100 mL) were added. The mixture was concentrated by rotary evaporation. The residue was dissolved in ethyl acetate (300 mL). The organic solution was washed with saturated aqueous sodium chloride solution (100 mL, containing excess solid sodium chloride). The aqueous layer was extracted with ethyl acetate (2*100 mL). The organic layers were combined and the combined solution was concentrated. Ether (100 mL) was added to the residue and the mixture was sonicated for 20 minutes during which time a white solid crashed out. The solids were collected by filtration. Ether (100 mL) was added to the collected solids and the mixture sonicated a second time. After 20 minutes, the mixture was filtered and the solids were collected to provide the title compound as a fine powder.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5,Some common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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.

Example 39(2,4-dichloro-3-phenylquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanolTo a flask containing 1 -methyl- lH-l ,2,3-triazole (125 mg, 1.5 mmol) was added THF (10 mL) and the colorless solution was cooled to -45 C. Then, -BuLi (2.5 M in hexaiies, 0,6 mL, 1.5 mmol) was added affordi g a suspension. The suspension was stirred between -40 C and -10 C for 30 minutes, then a THF solution of (2,4-dichloro-3-phenylquinolin-6-yl)(l,2-dimethyl-lH- imidazol-5-yl)niethanone (500 mg, 1.26 mmol, Intermediate 18: step b, in 5 mL THF) was introduced and the mixture was allowed to warm up to room temperature. After 1 hour, the reaction mixture was heated to 40 C for 3 hours and then quenched with aqueous NH4CI solution. The aqueous portion was extracted with EtOAc (3 x 50 mL) and then with DCM (3 x 50 mL). The individual organic portions were washed with brine, dried over MgS04, filtered, combined and concentrated to dryness. Chromatography on silica gel (5% MeOH-DCM increasing to 10% MeOH) provided material which was re -purified by preparative TLC (5% 2 M-NH3-MeOH-EtO Ac) to provide the title compound as light tan solid. H NMR (500 MHz,CDCI3) delta 8.45 – 8.36 (m, 1H), 7.94 (d, J= 8.8 Hz, IH), 7.66 – 7.46 (m, 4H), 7.46 – 7.30 (m, 2H), 7.01 (s, 1H), 5.94 (s, IH), 3.91 (s, 3H), 3.34 (s, 3H), 2.17 (s, 3H). MS (ESI): mass calcd. for C24H20CI2N6O, 478.1 , m/z found 479.1 [M+H]+.

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, belongs to Triazoles compound, 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 16681-65-5, Recommanded Product: 1-Methyl-1H-1,2,3-triazole

To a flask containing 1-methyl-1H-1,2,3-triazole (200 mg, 2.41 mmol) was added THF (15 mL) and the solution was cooled to -45 C. using a CH3CN-CO2 bath. n-BuLi (2.5 M in hexanes, 1.0 mL, 2.5 mmol) was added dropwise which afforded an opaque white suspension. The mixture was stirred at -45 C. for 25 minutes, then a solution of (4-chloro-3-cyclopentyl-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)methanone (475 mg, 1.24 mmol, Intermediate 68: step c) in THF (3 mL) was introduced. After 10 minutes, the -45 C. bath was replaced with an ice-water bath. After 30 minutes, the reaction mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc:THF (2:1, 3*40 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (3% MeOH-DCM increasing to 10% MeOH) provided the title compound as a light tan solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.24 (d, J=1.9 Hz, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.35 (dd, J=8.7, 2.0 Hz, 2H), 7.07 (s, 1H), 6.01 (s, 1H), 4.07 (s, 3H), 3.90-3.80 (m, 4H containing a 3H singlet at 3.86), 3.32 (s, 3H), 2.06-1.94 (m, 3H), 1.94-1.84 (m, 6H), 1.75-1.69 (m, 2H). MS (ESI): mass calcd. for C24H27ClN6O2, 466.2. m/z found 467.1 [M+H]+. The racemate was separated by chiral SFC (Stationary phase: Chiralpak AD-H, 5 mum 250¡Á20 mm, Mobile phase: 70% CO2: 30% EtOH (0.3% iPrNH2)) to give Example 135b as the first compound that eluted from the chiral column and Example 135c as the second compound that eluted from the chiral column.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, The chemical industry reduces the impact on the environment during synthesis 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, I believe this compound will play a more active role in future production and life.

Intermediate 52: step b 1-(4-(1-methyl-1H-1,2,3-triazole-5-carbonyl)piperidin-1-yl)ethanone A solution of i-memyl-lH-l ,2,3-triazole (0.28 g, 3.37 mmol) in dry THF (3 mL) was cooled in a -78 C bath and -butyllithium (2.5 M in hexanes, 1 .26 mL, 3.15 mmol) was added dropwise over a 20 minute period. The suspension was stirred in the cold bath for 30 minutes and then 1 – acetyl-A’-methoxy-N-methy}piperidine-4-carboxamide (0.74 g, 3.45 mmol, Intermediate 52: step a) dissolved in THF (3 mL) was added dropwise. The resulting suspension was stirred at -78 C for 5 minutes then warmed to 0 C and stirred for an additional 30 minutes. The mixture was warmed to room temperature and stirred for 2,5 hours then quenched with saturated aqueous NH4C . The aqueous mixture was extracted with EtOAc (2 x). The combined EtOAc extracts were dried over Na2S04, filtered, concentrated to dryness and chromatographed (EtOAc/DCM) to provide the title compound.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-1,2,3-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, Name is 1-Methyl-1H-1,2,3-triazole, 16681-65-5, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

intermediate 6: step a(1-methyl-1H-1,2,3-triazol-5-yl)(1-methyl-1H-imidazol-5-yl)methanolA solution of 1 -methyl- lH- l ,2,3-triazole (1 .47 g, 17.7 mmol, PCT Int. Appl. 2008098104) in 20 mL THF was cooled to -40 C in a dry-ice/acetonitrile bath. -Butyllithium (1.6 M in hexane, 10.2 mL, 16.3 mmol) was added dropwise via syringe and the mixture was stirred at -40 C for 30 minutes. A solution of 1 -methyl- 1 H-imidazole-5-carbaldehyde (1.50 g, 13.6 mmol) in 10 mL THF was then added and the mixture was stirred for 5 minutes, then was transferred to an ice/water bath. After 1 hour, the mixture was quenched by addition of saturated aqueous NPLCl, diluted with water, and extracted twice with EtOAc. The aqueous phase, which contained the title compound, was then concentrated. The residue wras purified by flash column chromatography (silica gel, gradient 3-10% MeOH-DCM) to afford the title compound as a light yellow foam.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARBAY, Kent; EDWARDS, James, P.; KREUTTER, Kevin, D.; KUMMER, David, A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald, L.; WOODS, Craig, R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell, D.; LEONARD, Kristi, A.; WO2015/57203; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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 16681-65-5. 16681-65-5

Analogous to the general method described in J. Org. Chem. 2004, 69, 8115, and Chem. Pharm. Bull, 1997, 1145. To a 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.00 g, 12.0 mmol, Intermediate 42, step a) was added THF (75 mL) and the solution was cooled between -40 to -20 C. To this colorless homogeneous solution was added n-BuLi (2.5 M in hexanes, 5.0 mL, 11.4 mmol) dropwise which afforded a dark brown viscous mixture. After stirring at 0 C. for 1 hours, a THF (10 mL) solution of 4-chlorobenzaldehyde (1.60 g, 11.4 mmol) was introduced and the reaction mixture began to be stirred freely and remained brownish. After 3 hours the reaction mixture was quenched by pouring into a saturated solution of NH4Cl and the aqueous portion was extracted with EtOAc (4¡Á50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil which solidified upon standing. The crude material was triturated with Et2O to provide the title compound as a brown solid.

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 1-Methyl-1H-1,2,3-triazole.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, its 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. 16681-65-5

Compound 6. To a solution of compound 4 (5 g, 60 mmol, 1 eq.) in THF (120 mL) was added LDA (2M in THF, 45 mL, 1.5 eq.) dropwise at -78 C under N2. After the mixture was stirred at -78 C for 1 h, compound 5 (6.33 g, 90.3 mmol, 6.7 mL, 1.5eq.) was added dropwise at -78 C. The mixture was stirred at -78 C for additional 2 h under N2. The reaction mixture was then poured into ice sat. NH4Cl (100 mL) and extracted with DCM (150 mL x 5). The combined organics were washed with brine (200 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2, petroleum ether/ethyl acetate (1:1 to 0:1)) to afford compound 6 as a yellow solid. 1H-NMR (CDCl3, 400 MHz) delta 7.61 (s, 1H), 4.16-4.12 (m, 1H), 4.11 (s, 3H), 2.82 (d, J = 5.1 Hz, 1H), 1.37 (tq, J = 4.9, 8.2 Hz, 1H), 0.78-0.66 (m, 2H), 0.57-0.48 (m, 1H), 0.42-0.30 (m, 1H).

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 16681-65-5.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16681-65-5 name is 1-Methyl-1H-1,2,3-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 19a: (3-(4-(1H-pyrazol-1-yl)benzyl)-4-chloro-2-methoxyquinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A solution of w-butyllithium in hexanes (2.5 M, 0.32 mL, 0.81 nimol) was added dropwise to a stirring solution of 1 -methyl- 1H- 1 ,2,3-triazole (70.4 mg, 0.848 nimol, prepared according to PCX Int. AppL, 2008098104) in tetrahydrofuran (1 mL) at -50 C. After 20 minutes, a solution (gently warmed with a heat, gun to dissolve the ketone starting material) of (3-(4-(lH-pyrazol-l – yl)benzyl)-4-chk>ro~2-methoxyquinolin-6-yl)(l,2-dimethyl-l H- (200 mg, 0.42 mmol, Intermediate 21 : step b) in tetrahydrofuran (1 mL) was added dropwise. After 5 minutes, the flask was allowed to warm to 23 C. After 20 minutes, water (1 mL) was added. The biphasic mixture was partitioned between saturated aqueous sodium chloride solution (25 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried with sodium sulfate. The dried solution was filtered. Silica gel (2 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash column chromatography purification. Elution with dichloro methane initially, grading to 10% methanol-dichloromethane provided the title compound which was further purified by RP-HPLC eluting initially with 5% acetonitrile-water (containing 0,05% trifluoroacetic acid), grading to 95% acetonitrile-water (containing 0.05% trifluoroacetic acid) to provide the title compound as a white solid after partitioning the purified material between dichioromethane-saturated aqueous sodium bicarbonate solution, separating the layers, drying the organic layer with sodium sulfate, filtering the dried solution, and concentrating the filtrate to dryness.lH NMR (400 MHz, CDC13) delta ppm 8.21 (s, IH), 7.85 (d, J = 2.4 Hz, I H), 7.74 (d, J = 8.8 Hz, 1H), 7.67 (d, J = 1.7 Hz, 1H), 7.60 – 7.53 (m, 2H), 7.41 – 7.33 (m, 3H), 7.11 (d, J = 1.4 Hz, IH), 6.46 – 6.39 (m, I H), 6.08 – 6.02 (m, IH), 4,27 (s, 2H), 4.08 (s, 3H), 3.89 (s, 3H), 3.35 (s, 3H), 2.20 (s, 3H); MS (ESI): mass calcd. for C29H27CIN8O2, 554.2; ni/z found, 555.2 j VI ¡¤ Pi | .(3-(4-(]J/-P Tazol-l-yl)benzyl)-4-cMyl)(l-methyl-lH-l ,2,3-triazo3-5-yl)methanol was purified by chiral SFC (Chiralpak AD-H, 5 muetaiota, 250 x 20 mm, mobile phase: 55% CO2, 45% methanol containing 0.03% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 19b: NMR (500 MHz, CDC3) delta ppm 8.17 (d, ./ 2.2 Hz, 1 H), 7.88 – 7.84 (m, 1H), 7.78 (d, ./ 8.7 Hz, 1 H), 7.70 – 7.66 (m, 1H), 7.61 – 7.55 (m, 2H), 7.41 – 7.34 (m, 3H), 7.18 (s, 1 H), 6.47 – 6.39 (m, 1H), 6.16 (s, 5 H), 4.32 (s, 2H), 4.10 (s, 31 1). 3.92 (s, 3H), 3.40 (s. 3H), 2.33 (s, 3H); MS { LSI}: mass calcd. for C29H27C3N8O2, 554.2; m/z found, 555.5 [M+H] and the second eluting enantiomer was Example 19c:JH NMR (500 MHz, CDCI3) delta ppm 8.18 (d, J 2.2 Hz, 1H), 7.85 (d, J = 2.5 Hz, I I I). 7.76 id. ./ = 8.8 Hz, 1 1 1). 7.68 (d, ./ = 1.7 Hz, I H), 7.61 – 7.55 (m, 2H), 7.42 – 7.34 (m, 31 1). 7.17 (s, IH), 6.43 (t, ./ 2.1 Hz, }. 6.13 (s, }. 4.31 (s. 2H), 4.10 (s. 3H), 3.91 (s, 3H), 3.39 (s, 3H), 2.31 (s, 3H); MS (ESI): mass calcd. for C29H27CIN8O2, 554.2; m/z found, 555.5 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-1,2,3-triazole, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, Kristi A.; BARBAY, Kent; EDWARDS, James P.; KREUTTER, Kevin D.; KUMMER, David A.; MAHAROOF, Umar; NISHIMURA, Rachel; URBANSKI, Maud; VENKATESAN, Hariharan; WANG, Aihua; WOLIN, Ronald L.; WOODS, Craig R.; FOURIE, Anne; XUE, Xiaohua; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 16681-65-5 name is 1-Methyl-1H-1,2,3-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 16681-65-5

The title compound was prepared according to No. WO2008 / 135826 International Patent Application Publication. In 1-methyl -1H-1,2,3- triazole (1.0g, 12.0 mmol, prepared according to International Patent Application No. 2008098104) 50 mL 2-neck flask containing, by the addition of THF (45 mL) , colorless solution was cooled to -40 . Then, by adding dropwise the (2.5 M, 4.8 mL, 12.0 mmol in hexane) n-BuLi, to give a dark reddish brown viscous solution. The mixture was stirred for 45 minutes at -30 to -20 in the following, was introduced into a pure DMF (3mL, 38.5 mmol) at -10 . The mixture was allowed to warm to room temperature, after stirring for 60 minutes, poured into water. Extract the aqueous portion with EtOAc (4 ¡Á 50 mL), the combined organics washed with brine, dried with MgSO4, filtered, and concentrated. The aqueous portion was extracted with DCM (3 ¡Á 50 mL) station, and dried as described above. The combined organics were concentrated to give a light brown oil The UV activity much higher than the starting material. DCM-25% CH3CN, according to TLC or of from 25% EtOAc-DCM, showed the product has a slightly higher Rf than the starting material. (With 100% DCM, 25% CH3CN-DCM increased) by silica gel chromatography on to give the title compound as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-1,2,3-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics