Category: imidazoles-derivatives

Related Products of 137049-00-4, A common heterocyclic compound, 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

To a 125 mL round-bottomed flask equipped with N2 inlet were added 302 mg (730 umol) N-t-butoxycarbonyl-(2-aza- bicyclo[3.3.1]non-6-yl)-(3-trifluoromethoxy-benzyl)-amine, 197 mg (1.09 mmol) N- methylimidazole-4-carbonyl chloride hydrochloride, 141 mg (1.09 mmol) diisopropylethylamine, and 10 mL dry acetonitrile. The reaction was heated at 800C for 72 hours, cooled, diluted with ethyl acetate, washed with aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated to an oil. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 198 mg (49%) of a mixture of isomers as an oil.13C-NMR (delta, CDCI3): 21.45, 24.04, 24.23, 24.31 , 24.58, 25.45, 27.24, 28.08, 28.60, 28.63, 30.59, 31.09, 31.22, 31.58, 32.63, 32.89, 33.72, 34.11 , 37.87, 39.38, 40.31, 42.85, 44.96, 46.02, 48.71, 48.98, 57.49, 61.47, 61.90, 79.51, 119.35, 119.58, 119.68, 119.80, 120.00, 120.16, 121.91 , 124.14, 125.56, 125.80, 126.02, 129.81 , 139.19, 141.11 , 142.03, 149.48, 155.55, 155.78 (a mixture of isomers).MS: 559 (parent+1 for MW = 558, C25H33N4O5SF3).HRMS Calc’d. for C25H34N4O5SF3: 559.2202. Found: 559.2178 (-4.3 ppm).

The synthetic route of 137049-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65500; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 36947-68-9,Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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.

Add 2-isopropyl imidazole (0.22 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After concentration, extraction, column chromatography separation, drying and the like, the intermediate VII-5 (0.53 g) is obtained, the yield is 85.3%; the white solid

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

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei¡¤lamohan¡¤laao¡¤yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 124750-92-1, 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 124750-92-1 as follows.

Step 3:; A solution of dicyclohexylcarbodiimide (DCC) (267.4 mg; 1.3 eq.) in anhydrous THF (10 ml) was added dropwise to a stirred solution of losartan acid (472 mg; 1.08 mmol) prepared as described in step 2, 5-(4-hydroxyphenyl)-3H-1,2-dithiol-3-thione (244.5 mg; 1.08 mmol) prepared as above described (step 1) and dimethylaminopyridine (DMAP, 7 mg) in 15 ml of tetrahydrofurane (THF). The reaction is performed at room temperature, stirring under nitrogen for 5 hours. At the end of the reaction the dicyclohexylurea (DCC) is removed by filtration. The solution is evaporated to dryness and the crude product was purified by column chromatography (on silica gel) eluting with CH2C12-methanol (97:3) to give an orange solid with melting point 180-185 C.

According to the analysis of related databases, 124750-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTG Pharma S.r.l.; EP1980559; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, category: imidazoles-derivatives

General procedure: To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (30 mL) containing piperidine (0.50 mL) either benzaldehyde (1.06 g, 0.01 mol) or 4-methoxy benzaldehyde (1.31 g, 0.01 mol) or 4-chlorobenzaldehyde (1.34 g, 0.01 mol) was added. The reaction mixture, in each case, was heated under reflux for 3 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Ethyl 2-(1H-benzo[d]imidazol-2-yl)-3-phenylacrylate (7a). Gray crystals from ethanol; yield:2.45 g (77%); m.p. > 300 oC. IR, : 3478-3329 (NH), 3057 (CH aromatic), 2962, 2873 (CH3,CH2), 1688 (C=O), 1646 (C=N), 1630 (C=C). 1H-NMR: : 1.14 (t, 3H, J = 7.66 Hz, CH3), 4.21(q, 2H, J = 7.66 Hz, CH2), 6.24 (s, 1H, CH=C), 7.29-7.38 (m, 9H, C6H5, C6H4), 8.26 (s, 1H, NH,D2O exchangeable). 13C NMR (DMSO): 16.3 (ester CH3), 52.5 (ester CH2), 89.3, 90.2 (CH=C),120.6, 122.1, 123.2, 123.9, 124.1, 124.6, 125.8, 126.2, 127.8, 128.2, (C6H5, C6H4), 164.8 (CO),172.6 (C=N); Anal. calcd for C18H16N2O2: C, 73.95; H, 5.52; N, 9.58%. Found: C, 72.73; H,5.49; N, 9.37%. MS: m/z: (%) 292 (M+, 64%).

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 2-(1H-benzo[d]imidazol-2-yl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 23328-88-3, 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. 23328-88-3 name is 2-Bromo-4-methyl-1H-imidazole, 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.

2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole (B) A mixture of 1,5-difluoro-3-methoxy-2-nitrobenzene (9 g, 47.6 mmol), 2-bromo-4-methylimidazole (7.7 g, 47.6 mmol) and potassium carbonate (14.5 g, 104.7 mmol) in 240 mL DMF was stirred at room temperature overnight. The majority of solvent was removed by rotavap and the residue was diluted with ethyl acetate and washed with water. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with water, brined, dried over magnesium sulfate. Condensation and purification using 5-10% ethyl acetate in dichloromethane as eluent provided 4.8 g (31% yield) of 2-bromo-1-(5-fluoro-3-methoxy-2-nitrophenyl)-4-methyl-1H-imidazole as a yellow solid. 1H NMR (400 MHz, DMSO) delta ppm 7.60 (dd, 1H), 7.38 (dd, 1H), 7.21 (s, 1H), 3.98 (s, 3H), 2.09 (s, 3H). EIMS 330.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; ELBION GMBH; WYETH; US2009/143367; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 111851-98-0, These common heterocyclic compound, 111851-98-0, name is 1-Ethyl-1H-imidazole-2-carbaldehyde, 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.

[00453] (¡ê)-3-(l-ethyl-lH-imidazol-2-yl)-l-(thiazol-2-yl)prop-2-en-l-one was prepared from l-(4-methylthiazol-2-yl)-2-(triphenyl- 5-phosphanylidene)ethan-l-one (1.0 equiv.) and 1 -ethyl- lH-imidazole-2-carbaldehyde5 via Wittig reaction (24 h) in 56 % isolated yield, using synthetic procedures described for the preparation of the analog SW209415. H NMR (400 MHz, CDCI3) delta 8.26 (d, / = 15.4 Hz, 1H), 8.03 (d, / = 3.0 Hz, 1H), 7.82 (d, / = 15.4 Hz, 1H), 7.67 (d, 7 = 3.0 Hz, 1H), 7.22 (s, 1H), 7.07 (d, 7 = 1.2 Hz, 1H), 4.15 (q, 7 = 7.4 Hz, 2H), 1.45 t, / = 7.3 Hz, 3H). ESI-MS (m/z): 234.1 [M+H]+.

Statistics shows that 1-Ethyl-1H-imidazole-2-carbaldehyde is playing an increasingly important role. we look forward to future research findings about 111851-98-0.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; READY, Joseph; ZHANG, Yongyou; ANTCZAK, Monika; WILLSON, James K.V.; POSNER, Bruce A.; GREENLEE, William; (254 pag.)WO2016/168472; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 41716-18-1, These common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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.

To a solution of intermediate 30-d (2.0 g, 3.73 mmol) in DMF, cooled to 0¡ã C., were sequentially added 1-methyl-1H-imidazole-4-carboxylic acid (564 mg, 4.47 mmol), HATU (1.70 g, 4.47 mmol) and DIPEA (2.60 mL, 14.91 mmol) and the reaction mixture was stirred at 0¡ã C. for 2 hours. Saturated aqueous ammonium chloride and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride, saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 31-a as a white foam

Statistics shows that 1-Methyl-1H-imidazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 41716-18-1.

Reference:
Patent; Pharmascience Inc.; Laurent, Alain; Proulx, Melanie; Rose, Yannick; Denissova, Irina; Dairi, Kenza; Jarvis, Scott; Jaquith, James B.; (189 pag.)US9284350; (2016); B2;,
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. 15813-09-9, name is 4,5-Diiodo-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H2I2N2

A mixture of 2 (12.0 g, 37.5 mmol)and Na2SO3 (23.6 g, 187.3 mmol) in EtOH (120 mL) and H2O (20 mL)was refluxed for 72 h. The mixture was concentrated in vacuo andthe residue was extracted with ethyl acetate. The crude productwas purified by recrystallization from dichloromethane to afford 3as a white solid (3.5 g, 48.1%). Mp 137e139 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 7.0 (s, 1H), 7.5 (s, 1H). MS (EI) m/z 194.9[MH].

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 15813-09-9.

Reference:
Article; Zou, Yi; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; Li, Yuezhen; Liu, Wen; Guo, Wenjie; Huang, Zhangjian; Zhang, Yihua; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 293 – 304;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1450-93-7, name: 1H-imidazol-2-amine sulfate(2:1)

EXAMPLE 13 7-Methyl-5-[3-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine A mixture of 5.14 g of (3-dimethylamino)-1[3-(trifluoromethyl)phenyl]-2-butene-1-one, 1.64 g of anhydrous sodium acetate and 2.64 g of 2-aminoimidazole hemisulfate in 100 ml of glacial acetic acid was refluxed for six hours. The solvent was removed in vacuo and the solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was separated and dried over powdered anhydrous sodium sulfate, then passed through a short column of a hydrous magnesium silicate. The effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling the product was separated and collected by filtration and gave 2.55 g of the desired compound as off-white crystals, m.p. 170-172 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-imidazol-2-amine sulfate(2:1), and friends who are interested can also refer to it.

Reference:
Patent; American Cyanamid Company; US5037980; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1219741-19-1, 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. 1219741-19-1 name is 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, 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.

To a suspension of 6-chloro-5-iodo-2-(methylsulfonyl)-lH-benzo[d]imidazole (5.042 g, 14.14 mmol) in DCM (100 mL) at 0C was added TEA (2.96 mL, 21.21 mmol), and SEM-C1 (2.76 mL, 15.55 mmol) dropwise. The resulting solution was stirred from 0C for 1 hr. The reaction mixture was partitioned between water (200 mL) and DCM (100 mL), the aqueous phase was extracted with DCM (200 mL), and the combined organic phase was dried over anhydrous Na2S04, concentrated and the residue was purified on silica gel column using EtOAc/hexane as eluting solvents to give the title compound. LC/MS: (M+l) : 487.17.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-6-iodo-2-(methylsulfonyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem