Author: Jessica.F

Application of 39070-14-9, These common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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.

Phenstatin (0.500 g, 1.57 mmol), (1-methyl-2-nitro-1H-imidazol-5-yl)methanol (0.296 g, 1.89 mmol), and DIAD (0.40 mL, 2.04 mmol) were dissolved in CH2Cl2. Triphenylphosphine (0.825 g, 3.14 mmol) was added to the mixture, and the reaction mixture was stirred for 24 h. The reaction mixture was then evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 100 g silica column [eluents: solvent A: EtOAc; solvent B: hexanes; gradient, 17%A/83%B over 1.19 min (1 CV), 17%A/83%B 100%A/0%B over 8.33 min (7 CV), 100%A / 0%B over 5.95 min (5 CV); flow rate 100 mL/min; monitored at 254 and 280 nm] yielded (4-methoxy-3-((1-methyl-2-nitro-1H-imidazol-5-yl)methoxy)phenyl)(3,4,5-trimethoxyphenyl)methanone (31) as a pale yellow-white solid (0.346 g, 0.757 mmol, 48%) [0.284 g, 0.621 mmol, 39%, corrected for EtOAc].1H NMR (600 MHz, CDCl3) delta 7.62 (1H, d, J = 1.7 Hz), 7.52 (1H, dd, J = 8.3, 1.7 Hz), 7.24 (1H, s), 7.04 (2H, s), 6.97 (1H, d, J = 8.4 Hz), 5.18 (2H, s), 4.16 (3H, s), 3.97 (3H, s), 3.96 (3H, s), 3.91 (6H, s).13C NMR (151 MHz, CDCl3) delta 194.16, 153.97, 152.91, 146.74, 141.88, 132.92, 132.30, 130.43, 129.31, 127.00, 116.43, 110.61, 107.52, 99.98, 61.24, 61.01, 56.39, 56.05, 34.54.HRMS [M+Na]+: 480.1376 (calcd for [C22H23N3NaO8]+,480.1377).HPLC retention time (Method B): 4.66 min [100% at 254 nm].

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Winn, Blake A.; Shi, Zhe; Carlson, Graham J.; Wang, Yifan; Nguyen, Benson L.; Kelly, Evan M.; Ross, R. David; Hamel, Ernest; Chaplin, David J.; Trawick, Mary L.; Pinney, Kevin G.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 3; (2017); p. 636 – 641;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 19225-92-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 19225-92-4, name is 2-(Chloromethyl)-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 50; N-{5-amino-3-cyano-1- [2, 6-dichloro-4-pentafluorothiophenyl]-1 H-pyrazol-4-yl}-N [ (1- methyl-1 H-imidazol-2-yl) methyl] methanesulfonamide; To a mixture of Example 38 (200 mg, 0.42 mmol) and 1- (N-methyl)-2- chloromethylimidazole (106 mg, 0.64 mmol) in acetonitrile (12 ml) was added potassium carbonate (116 mg, 0.84 mmol). The reaction mixture was then stirred at 40C for 18 h. To the reaction mixture was added water (6 mi) and ethyl acetate (10 ml). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 5 ml). The combined organic phases were then dried (MgS04) and concentrated in vacuo. The residue was dissolved in acetonitrile/water (3 mi) and the solution was purified by automated preparative liquid chromatography (Gilson system, 150 x 50 mm, LUNA II C18 10 zm column) using an acetonitrile : water gradient [45: 55 to 95: 5]. The appropriate fractions were concentrated to give the titled compound (98 mg). Experimental MH+ 565.9 ; expected 566.0 ‘H-NMR (CDC13) : 2.88-2. 91 (3H), 3.70-3. 74 (3H), 4.80-5. 03 (2H), 6.09-6. 18 (2H), 6.87-6. 89 (1 H), 6.92-6. 95 (1 H), 7.87-7. 90 (2H)

The synthetic route of 2-(Chloromethyl)-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: To a well-stirred solution of compound 1 (10mmol) and triethylamine (0.5mL) in acetone, benzenesulfonyl chloride, 4-toluenesulfonyl chloride or 2-nitrobenzenesulfonyl chloride (10mmol) was added dropwise. The reaction mixture was stirred for 2h at room temperature and left overnight. The solvent was evaporated under reduced pressure. The solid was collected, washed with water, dried. Purification by column chromatography was achieved using ethyl acetate/pet. ether (3:1 ratio) as the mobile phase.4.1.3.2 N-(4-(1H-Benzo[d]imidazol-2-yl)phenyl)-4-methylbenzenesulfonamide (8) Yield: 82%. Mp: 230-232 C, Rf = 0.60 (ethylacetate/pet. ether, 2:1). IR (KBr) numax/cm-1: 3373 (NH aminophenyl); 3061 (CH arom); 2922 (CH aliph); 1610 (C=N); 1596 (C=C arom); 1438 (nuas SO2), 1375 (nus SO2). 1H NMR (DMSO-d6, 500 MHz, delta ppm): 2.30 (s, 3H, CH3); 7.07 (d, 2H, J = 9.2 Hz, H2′, H6′ aminophenyl); 7.34 (m, 2H, H3and H5 tosyl); 7.43 (m, 2H, H2 and H6 tosyl); 7.71 (m, 2H, H5, H6 benzimidazole); 7.84 (m, 2H, H4, H7 benzimidazole); 8.01 (d, 2H, J = 9.2 Hz, H3′, H5′ aminophenyl); 10.91 (s, 1H, NH sulfonamide, D2O exchangeable). 12.75, (s, 1H, NH, benzimidazole, D2O exchangeable). MS, m/z (%):363 (M+, 14%); 347 (50%); 208 (100%). Anal. Calcd for C20H17N3O2S (FW: 363): C, 66.10; H, 4.71; N, 11.56; S, 8.82. Found: C, 66.42; H, 4.95; N, 11.14; S, 8.33.

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 2963-77-1.

Reference:
Article; Galal, Shadia A.; Khattab, Muhammad; Andreadaki, Fotini; Chrysina, Evangelia D.; Praly, Jean-Pierre; Ragab, Fatma A.F.; El Diwani, Hoda I.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5423 – 5430;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 144690-33-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 144690-33-5, name is Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 236.0 g (50.3 mmol) ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)-phenyl]phenyl}-methyl imidazole-5-carboxylate (Va) and 3.0 g (75.4 mmol) of NaOH were suspended in 413 ml dimethylacetamide. The suspension was then stirred at room temperature for 20 h and after that 6.9 g (50.3 mmol) of K2CO3, were added. The mixture was cooled to 0 C. and solution of 15.4 g (70.4 mmol) 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolene in 39 ml of dimethylacetamide were slowly added. The mixture was slowly heated to 50 C. and stirred at this temperature for 2 h. After esterification was completed, the mixture was cooled to 10 C. and poured into a mixture of 625 ml of ethyl acetate and 625 ml of 10% NaCl, and stirred at 25 C. for 15 min. The phases were separated and organic phase was washed 2× with 500 ml of 10% NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated up to ½ (approximately 270 g) at reduced pressure.To the resulting solution, 80 ml of ethanol and 8.3 ml (100 mmol) of conc. HCl were added and stirred at 24-26 C. for 3 h. To the cooled mixture 600 ml of water was added and pH of the suspension was estimated to 5 by addition of 5 M NaOH. The phases were stirred for 15 min and separated. Water phase was reextracted with 150 ml of ethyl acetate. Collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. 560 ml of ethyl acetate were added and the mixture was evaporated again. After that, 300 ml of ethyl acetate were added and the mixture was cooled to 20 C. and stirred for 1 h, filtered off and washed with 20 ml of fresh ethyl acetate. The yield of the product (I) was 21 g (75%).

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, Ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2′-(1-trityl-1H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KRKA; US2009/131680; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, belongs to imidazoles-derivatives 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 33468-69-8, Recommanded Product: 33468-69-8

Production Example 58A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.18 g of 4-(trifluoromethyl)-lH-imidazole, 0.55 g of potassium carbonate and 2 ml of DMF was stirred while heating at 50C for 1.5 hours. Then, the reaction mixture was cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.40 g of 2-{3-[4-(trifluoromethyl)imidazole-l-yl]pyridin-4-yl}-5-(trifluoromethyl)benzoxazole hereinafter, referred to as “active compound 57”).Active compound 571H-NMR (CDC13) delta: 9.00 (d, J=5.2 Hz, 1H), 8.84 (s, 1H), 8.31 (d, J=5.1 Hz, 1H), 8.06-8.04 (m, 1H), 7.77-7.75 (m, 1H), 7.74-7.70 (m, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.52-7.50 (m, 1H)

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, 4-(Trifluoromethyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49222; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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.

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H9F3N2O2

3-(4-Methyl-imidazol-l-yl)-N-{4-methyl-3-[3-methyl-3-(7H-pyrrolo[2,3- d1pyrimidin-4-ylVureido1-phenvU-5-trifluoromethyl-benzamide [00104] To a solution of 7 (7 mg, 0.23 mmol, 1.0 eq.), 3-(4-Methyl-imidazol-l- yl)-5-trifluoromethyl-benzoic acid (7.6 mg, 0.27 mmol, 1.2 eq.), and DIPEA (40 mul, 0.27 mmol, 1.2 eq.) in DMF (0.5 ml) is added HATU (9.9 mg, 0.25mmol, 1.1 eq.). After stirring for 1 hour at room temperature, the solvent is removed under vacuum. The residue is dissolved in DMSO (ImI). The resulting solution is subjected to purification by reverse- EPO phase LC-MS to yield the title compound as a TFA salt: 1H NMR 400 MHz (DMSOd6) delta 1H NMR 400 MHz (DMSOd6) delta 12.81 (bs, IH), 12.28 (bs, IH), 10.52 (bs, IH), 9.40 (s, IH), 8.52 (s, IH), 8.51 (s, IH), 8.40 (d, J = 2.0 Hz, IH), 8.36 (s, IH), 8.33 (s, IH), 7.48 (m, 2H), 7.19 (d, J = 8.32 Hz, IH), 6.78 (m, IH) 3.05 (s, 3H), 2.30 (s, 3H) 2.27 (s, 3H); MS m/z 549.2 (M + 1).

The synthetic route of 641571-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM, LLC; WO2006/124462; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 693-98-1, name is 2-Methyl-1H-imidazole, belongs to imidazoles-derivatives 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 693-98-1, name: 2-Methyl-1H-imidazole

Under a protection of N2, 0.25 mol of potassium carbonate, 0.5 mol of 2-methylimidazole and 0.6 mol of acrylonitrile were added to 60 mL of anhydrous methanol in a 250 ml three-neck round bottom flask, and the mixture was stirred under reflux in an oil bath at 60 C for 12 h. Complete reaction; After the reaction was stopped, the unreacted raw materials and methanol were removed by rotary evaporation, and dried under vacuum at 70 C for 24 hours to obtain a yellow transparent liquid. It is 1-nitrileethyl-2-methylimidazole. The yield was 82%.

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

Reference:
Patent; Hebei University of Technology; Zhang Wenlin; Wang Yuxin; He Jiaming; Zhao Yongqi; Huo Yu; Li Chunli; (12 pag.)CN108976169; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 288-32-4, These common heterocyclic compound, 288-32-4, name is 1H-Imidazole, 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.

General procedure: For the catalysis reaction, the catalyst C1 (12 mg,0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gou, Gao-Zhang; Wu, Na; Zhang, Ju-Cheng; Shi, Ling; Liu, Gui-Yang; Liu, Wei; Mang, Chao-Yong; Chi, Shao-Ming; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical; vol. 57A; 2; (2018); p. 181 – 185;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3314-30-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Adding clinfloxacin (500 mg, 1.37 mmol) to a 150 mL round bottom flask,Diethyl phosphite (451.28 mg, 4.10 mmol), benzimidazole-2-carbaldehyde (299.40 mg, 2.05 mmol) and toluene (50 mL) were stirred and refluxed at 120 C for 6 hours, and thin layer chromatography was followed until the reaction was completed. . After concentration, extraction, column chromatography separation,After recrystallization, drying, etc., the compound I-11 is obtained.(297.46 mg). Yield: 34.4%; yellow powder;

The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazole-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Southwest University; Zhou Chenghe; Wang Liangliang; Xu Jiahe; Zhao Wenhao; Ba Tini·nasaiya; (19 pag.)CN110041368; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem