Tag: M.W=100-200

Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41716-18-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 72-40-2,Some common heterocyclic compound, 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, molecular formula is C4H7ClN4O, 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.

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5 hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

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

Reference:
Patent; Benkovic, Stephen J.; Shapiro, Lucy; Wright, Rachel; Stephens, Craig; Kahng, Lyn Sue; Berdis, Anthony; Lee, Irene; US2005/227933; (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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

The tetrol derivative (compound 2.6) of 3a, 6a- cyclopentanoglycoluril (1 g, 3.3 mmol) was added to a solution of unsubstituted glycoluril (937 mg, 6.6 mmol) in conc. HCL (2 mL) and the mixture stirred at room temperature for 30 min. The homogeneous mixture was poured into MEOH (10 mL) and the precipitate collected and dried to give predominantly the trimer.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNISEARCH LIMITED; WO2005/26168; (2005); A1;,
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

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

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

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

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

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

Reference of 66121-69-5, 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 66121-69-5 as follows.

After dissolving 1-methylimidazole-4-carbonitrile (1.0 g, 8.0 mmol) in DMF (30 mL), trifluoroacetic hydrazide (1.9 g, 14.8 mmol)After adding and stirring at room temperature for 30 minutes.After adding sodium methoxide (28% methanol solution) to the reaction mixture, the mixture was raised to 140 C and stirred with heating for 48 hours.The reaction mixture was cooled to room temperature, the solvent was blown out, and then extracted with ethyl acetate and water. The organic layers are collected, dehydrated with sodium sulfate, the solids are filtered off and the solvent is blown off. The reaction mixture was purified using silica gel column chromatography to obtain compound (4).(0.35 g, 1.6 mmol) is obtained with a yield of 20%.

According to the analysis of related databases, 66121-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Electronics Co., Ltd.; Cheil Industries Inc.; Pusan National University Institute for Research & Industry Cooperation; Noh Chang-ho; Yoon Ung-chan; Kwon O-hyeon; Choi Byeong-gi; (23 pag.)KR102046153; (2019); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem