Author: Jessica.F

Electric Literature of 89830-98-8,Some common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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.

A suspension 2-chloro-5-fluoro-4-iodopyridine (1.8 g, 1.00 mmol), 4-cyclopropyl imidazole (982 mg, 9.10 mmol), Cu2O (100 mg, 0.700 mmol), 8-hydroxyquinoline (152 mg, 1.05 mmol), cesium carbonate (4.60 g, 14.0 mmol), and PEG-3350 (1.4 g) in butyronitrile (50 mL) was heated at 65 C. for 16 hours. The reaction mixture was filtered through Celite, concentrated and the residue was partitioned between dichlormethane and water. The layers were separated and the aqueous layer washed twice with dichloromethane. The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (15?60% EtOAc in hexanes) to afford 2-chloro-4-(4-cyclopropyl-1H-imidazol-1-yl)-5-fluoropyridine (702 mg, 42% yield).

The synthetic route of 89830-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Sciences, Inc.; Notte, Gregory; US2014/179663; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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 6160-65-2, Recommanded Product: 1,1′-Thiocarbonyldiimidazole

A solution of the amine (0.110 g, 0.43 mmol) in anhydrous CH2Cl2 (2 mL) was added dropwise over 2-5 minutes to an ice-salt bath cooled solution of 1,1?-thiocarbonyldiimidazole (95%, 0.162 g, 0.87 mmol, 2 eq.) in anhydrous CH2Cl2 (6 mL). After 15 minutes, the cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours after which time analysis by TLC (10% MeOH in CH2Cl2) indicated complete consumption of the starting aniline. The mixture was cooled once again in an ice bath and 7 M NH3 in MeOH (620 muL, 4.3 mmol, 10 eq.) was added dropwise over 2-5 minutes. The bath was removed and the mixture was stirred over night at room temperature. Silica gel (1 g) was added and the mixture was concentrated to dryness under reduce pressure. Flash column chromatography (RediSepRf SiO2 (40 g), 100% CH2Cl2?10% MeOH in CH2Cl2) gave the thiourea as an amber oil that solidified upon standing (0.130 g, 97%).

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, 1,1′-Thiocarbonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Duke University; Liedtke, Wolfgang; (96 pag.)US2016/199363; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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. category: imidazoles-derivatives

(1) Ethyl 5-methyl-1H-imidazole-4-carboxylate (Sigma-Aldrich Co., Ltd.) (7.5g, 48.7mmol) in acetonitrile (120mLWas dissolved in), there N-bromosuccinimide (10.4g, 58.4mmol) added The mixture was stirred at room temperature for 3 hours on. After the reaction, a saturated sodium hydrogen carbonate aqueous solution was added, with ethyl acetateIt was extracted twice. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. concentratedAfter it was purified by column chromatography, ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51605-32-4, its application will become more common.

Reference:
Patent; TEIJIN PHARMA LIMITED; MARUYAMA, AKINOBU; KAMADA, HIROFUMI; FUJINUMA, MIKA; TAKEUCHI, SUSUMU; SAITO, HIROSHI; TAKAHASHI, YOSHIMASA; (95 pag.)JP2015/214527; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2301-25-9, These common heterocyclic compound, 2301-25-9, name is 1-(4-Nitrophenyl)-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.

10.0 g of 4-(imidazole-1-yl)nitrobenzene were dissolved in 80 ml of acetic acid, and 35.1 g of anhydrous tin(II) chloride were subsequently added to the resultant solution. The solution was then stirred for 3 hours at 90-95 C. After cooling the solution reacted and removing the solvent used by distillation under reduced pressure, pH of the solution was adjusted to a range of from 9 to 11 with 10% aqueous solution of NaOH to extract the solution with chloroform. After dried the organic layer resulted with anhydrous magnesium sulfate, the solvent used was removed by distillation under reduced pressure, thereby affording 7.2 g of 4-(imidazole-1-yl)aniline.

Statistics shows that 1-(4-Nitrophenyl)-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 2301-25-9.

Reference:
Patent; Nippon Soda Co., Ltd.; US5965743; (1999); A;,
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. 16042-25-4, name is 2-Imidazolecarboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Imidazolecarboxylic acid

The mixture of H3PMo12O40·26H2O (0.2g, 0.07mmol), AgNO3 (0.08g, 0.47mmol), and L1 (0.049g, 0.2mmol) was dissolved in 10mL of distilled water and stirred for 45mins at room temperature. The pH value was adjusted to 1.80 with 1.0molL-1 HNO3 (final pH 1.95). Then, the suspension was sealed into a Teflon-lined stainless steel autoclave (25mL) and kept under autogenous pressure at 160C for 3days. Slow cooling of the reaction mixture to room temperature, yellow block crystals were filtered and washed with distilled water (42% yield based on Mo). Elemental Anal. Calc. for C16H19Ag2N8O51PMo12 (2537.29): C 7.56, H 0.75, N 4.41. Found: C 7.60, H 0.72, N 4.39%

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 16042-25-4.

Reference:
Article; Tian, Ai-Xiang; Hou, Xue; Ying, Jun; Liu, Guo-Cheng; Ning, Ya-Li; Li, Tian-Jiao; Wang, Xiu-Li; Inorganica Chimica Acta; vol. 439; (2016); p. 43 – 48;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 172499-76-2, 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. 172499-76-2 name is Ethyl 3-(1H-imidazol-2-yl)propanoate, 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.

4-Chloro-1-fluoro-2-nitrobenzene 1.04 g, ethyl 3-(1H-imidazol-2-yl) propanoate 1,00 g, potassium carbonate 1.64 g and N,N-dimethylacetamide 20 mL were mixed and heated in nitrogen atmosphere at 100C for 12 hours. The reaction liquid was diluted with ethyl acetate, and water was added to induce phase separation. The organic layer was washed with saturated brine, dried over sodium sulfate and removed of the solvent by distillation. Thus obtained compound was dissolved in 10 mL of acetic acid and 10 mL of water and to which 6.00 g of 85% sodium hydrosulfite was added, followed by 2 hours’ heating under reflux. The reaction liquid was cooled with ice and neutralized with saturated aqueous sodium hydrogencarbonate solution. Extracting the same with ethyl acetate, the extract was washed with saturated brine, dried over sodium sulfate and removed of the solvent by distillation. The resulting compound was mixed with 1,4 g of 1,1′-carbonyldiimidazole and 20 mL of 1,2-dichlorobenzene and heated under reflux for 5 hours in nitrogen atmosphere. The solvent was distilled off and methanol was added, followed by an overnight’s stirring. The precipitated crystals were recovered by filtration, washed with methanol and dried in flowing air to provide 530 mg of the title compound. 1H-NMR(DMSO-d6, delta): 1.19(3H, t, J=7.1Hz), 2.96(2H, t, J=6.5Hz), 3.48(2H, t, J=6.7Hz), 4.08(2H, q, J=7.3Hz), 7.30(1H, dd, J=2.3, 8.8Hz), 7.35(1H, d, J=2.3Hz), 7.78(1H, s), 8.05(1H, d, J=8.8Hz), 11.45(1H, s). MS(m/z): 321(M++2), 319(M+).

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

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP2103613; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 36947-68-9, name is 2-Isopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H10N2

To 2-isopropylimidazole (28mg) in dry N,N-dimethylformamide (ImI) was added sodium hydride (lOmg, 60% dispersion in mineral oil). After 30 minutes, 2-chloro-6- (4-methanesulfonyl-piperazin-l-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine, prepared via General Procedure B-3, was added and the reaction mixture was heated in the microwave for 45 minutes at 12O0C. The reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and the solvent removed in vacuo and the residue purified using flash chromatography to yield 176. NMR (400MHz CDC13): 1.19(lH,s,CH), 1.30(6H,d(J=6.84), 2.61-2.63(4H,m,CH2), 2.74(3H,s,CH3), 3.23-3.25(4H,m,CH2), 3.79- 3.82(6H,m,CH2), 3.92-3.94(4H,m,CH2), 6.92(lH,s,ar), 7.18(lH,s,ar), 7.66(lH,d(J=1.49),ar). MH+ 506.30

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; PIRAMED LIMITED; GENENTECH, INC.; BAYLISS, Tracy; CHUCKOWREE, Irina; FOLKES, Adrian; OXENFORD, Sally; WAN, Nan, Chi; CASTANEDO, Georgette; GOLDSMITH, Richard; GUNZNER, Janet; HEFFRON, Tim; MATHIEU, Simon; OLIVERO, Alan; STABEN, Steven; SUTHERLIN, Daniel, P.; ZHU, Bing-Yan; WO2008/70740; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 72-40-2, These common heterocyclic compound, 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, 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 stirred solution of 4-aminoimidazole-5-carboxamide hydrochloride [0957] (1 g, 6.151 mmol) in N,N-dimethylformamide (5 mL) was added ethylxanthic acid potassium salt (1.479 g, 9.226) and the mixture was heated at 140 C. for 5 h. The reaction mixture was concentrated under reduced pressure. The residue was triturated with acetonitrile (20 mL). The solid was filtered, washed with acetonitrile (10 mL) and dried under vacuum to afford 2-mercapto-1,9-dihydro-6H-purin-6-one [0958] as a brown solid (0.8 g, 77%). MS(M+1)+=169.0.

The synthetic route of 72-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cadent Therapeutics, Inc.; Jefson, Martin R.; Keaney, Gregg F.; Larsen, Janus Schreiber; Lowe, III, John A.; McCall, John M.; (110 pag.)US2017/355708; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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.

The bisbenzimidazole heterocyclic compound(500 mg, 1.64 mmol) was dissolved in 20 mL of N, N-dimethylformamide,Sodium hydride (79 mg, 3.3 mmol) was added,Stirred at room temperature for 30 min,A solution of N, N-dimethylformamide (10 mL) containing N-o-methoxycarbonylphenyl-4-bromomethylindole (617 mg, 1.8 mmol) was slowly added dropwise.After dripping,The mixture was stirred at room temperature for about 2 h,TLC was monitored until the reaction was complete.Add 2M sodium hydroxide solution 2mL,Stir at room temperature for about 2 h.TLC monitoring to the reaction is complete,The pH was adjusted to 5-6 with 2M hydrochloric acid, 200 mL of dichloromethane and 200 mL of 7 K were added to the reaction solution,Take the organic phase,The aqueous phase was extracted three times with dichloromethane (150 mL X3)Combine the organic phase.The organic phase was washed four times with saturated brine (300 mL X4)Dried over anhydrous magnesium sulfate,filter,The solvent was distilled off under reduced pressure,To give a tan solid.The solid was recrystallized to give about 600 mg (yield: about 66.0%) of the off-white solid product.

Statistics shows that 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole is playing an increasingly important role. we look forward to future research findings about 152628-02-9.

Reference:
Patent; Chen, Zhilong; Zhu, Weibo; Ren, He; Yan, Yijia; Bao, Xiaolu; Chen, Danye; (16 pag.)CN106467521; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 144689-93-0

Ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-imidazole-5-carboxylate (100 gm) was dissolved in acetone (2500 ml) and then added potassium carbonate (100 gm), 5-[4′-(bromomethyl)[1,1′-biphenyl]-2-yl]-2-(triphenylmethyl)-1H-tetrazole (250 gm) and tert-butyl ammonium bromide (15 gm) under stirring at room temperature. The temperature of the reaction mass was raised to 50 to 55 C. and maintained for 15 hours at 50 to 55 C. The reaction mass was cooled to 45 C. and passed over celite bed. The collected filtrate was cooled to 0 to 5 C. and then added a solution of potassium carbonate (36 gm) in water (36 ml) for 1 hour. The temperature of the reaction mass was raised to room temperature and maintained for 16 hours at room temperature. The acetone was distilled off completely under vacuum at below 40 C. to obtain residue. To the residue was added sodium chloride solution (10%, 900 ml) and then added ethyl acetate (1500 ml). The layers were separated and the aqueous layer was extracted. Combined the both organic layers and dried over sodium sulfate. The solvent was distilled off completely to obtain a residual mass. A mixture of acetone (1200 ml), potassium carbonate (100 gm), (4-bromoethyl)-5-methyl-oxo-1,3-dioxane (105 gm) and potassium iodide (17 gm) were added under stirring at room temperature and then the contents were heated to 50 to 55 C. The solution was added to the above residual mass for 1 hour 30 minutes and maintained for 1 hour 30 minutes at 50 to 55 C. The reaction mass was cooled to 45 C. and filtered. The solvent was distilled off completely to obtain residue. Toluene (1500 ml) was added to the residue and the layers were separated. The toluene layer was dried over sodium sulfate and distilled off the layer under vacuum up to obtain clear residual mass. To the residual mass was added methanol (1500 ml) and stirred for 30 minutes at room temperature. The reaction mass was cooled to 10 to 15 C. and maintained for 1 hour 30 minutes. The separated solid was filtered and dried at 40 to 45 C. for 7 hours to obtain 270 gm of trityl olmesartan medoxomil. Trityl olmesartan medoxomil: 98.5%; Trityl olmesartan ethyl ester impurity: 0.35%; Bromo trityl olmesartan medoxomil impurity: 0.35%; Methyl trityl olmesartan medoxomil impurity: 0.34%.

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HETERO RESEARCH FOUNDATION; Parthasaradhi Reddy, Bandi; Rathnakar Reddy, Kura; Muralidhara Reddy, Dasari; Raji Reddy, Rapolu; Ramakrishna Reddy, Matta; Vamsi Krishna, Bandi; US2013/190506; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem