Month: September 2021

Synthetic Route of 40644-16-4,Some common heterocyclic compound, 40644-16-4, name is 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H5BrN2O, 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.

Step 3: 4-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol- 2-one To a solution of 4-bromo-1 ,3-dihydro-benzoimidazol-2-one (701 mg, 3.29 mmol) in dimethyl sulfoxide (2 ml_) was added potassium acetate (803 g, 10.9 mmol), 1,1′-bis(diphenyl phosphino) ferrocene palladium chloride (PdCI2 (dppf)) (134 mg, 0.16 mmol) and bis(pinacolato) diboron (1.67 g, 6.58 mmol). The mixture was degassed and heated in a microwave oven for 30 minutes at 150 0C. The solvent was filtered through a pad of celite, water (60 ml_) was added and the product was extracted with EtOAc (3 x, 30 ml_). The combined organic extracts were dried over Na2SO4 (sodium sulfate), and the solvent removed to provide crude 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1 ,3-dihydro-benzoimidazol-2-one which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Patent; WYETH; WO2009/111260; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 51605-32-4, A common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

Ethyl 4-methyl-1 H-imidazole-5-carboxylate (463 mg, 3.00 mmol, 1 eq) was combined with iodomethane (0.19 mL, 3.00 mmol, 1 eq) and potassium carbonate (828 mg, 6.00 mmol, 2 eq) in acetonitrile and stirred overnight at reflux. The reaction mixture was cooled to ambient temperature, inorganics filtered off, and the filtrate concentrated to dryness. The residue was purified on an 80 g silica gel cartridge eluted with 100percent EtOAc to 10percent CH3OH/DCM to give the two regioisomeric products. The first eluting isomer was identified as the title compound (185 mg, 1.95 mmol, 35percent) by comparative NOESY and HMBC NMR. 1 H NMR (400 MHz, DMSO- d6) delta ppm 7.74 (s, 1 H), 4.25 (q, J=7.14 Hz, 2 H), 3.76 (s, 3 H), 2.34 (s, 3 H), 1.30 (t, J=7.10 Hz, 3 H). LC-MS (ES+) m/z 169.08 [M+H]

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); 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. 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1,3-dihydrobenzoimidazol-2-one

5-Bromo-1,3-dihydrobenzimidazol-2-one (1.30 g, 6.10 mmol), 1-tert-butoxycarbonyl-2,5-dihydro-1H-pyrrole-3-boronic acid pinacol Ester (1.77 g, 6.00 mmol), 1,1′-bisdiphenylphosphinoferrocene palladium dichloride (230 mg,0.314 mmol) and potassium carbonate (2.49 g, 18.0 mmol) were mixed in N,N-dimethylformamide (30 mL).The oxygen was replaced by nitrogen, and then heated to 100 C for 16 hours.The reaction system was diluted with ethyl acetate (300 mL), and the organic phase was washed with water (100 mL×2).The mixture was washed with saturated brine (100 mL × 5) and dried over anhydrous sodium sulfate.The desiccant was removed by filtration, and the solvent was concentrated under reduced pressure.Column chromatography purification (petroleum ether / ethyl acetate / ethanol = 12 / 3 / 1, 3 / 3 / 1),A pale yellow solid (300 mg, yield 17%) was obtained.

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 39513-26-3.

Reference:
Patent; Maidikang (Shanghai) Bio-pharmaceutical Technology Co., Ltd.; Dang Zhu; Ke Lisiting·juecai; Luo Zhen; Wang Liugang; Bao Dan; Qi Tafamingrenqingqiubugongkaixingming; (106 pag.)CN109956931; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

103057-10-9, name is 4-(Chloromethyl)-1-trityl-1H-imidazole, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 4-(Chloromethyl)-1-trityl-1H-imidazole

Step H 4-Diethylphosphonomethyl-1-triphenylmethylimidazole The product from Step G is dissolved in acetonitrile and cooled to 0 C. Triethyl phosphite (1 equivalent) and sodium iodide (1 equivalent) were added, and the reaction stirred at room temperature overnight. The reaction is quenched with ammonium chloride, and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated to provide the title compound.

The synthetic route of 103057-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5965578; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71%) was obtained as a white solid.

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, A new synthetic method of this compound is introduced below., Safety of 4-Imidazolemethanol hydrochloride

0.2 Mol 4-hydroxymethyl imidazole hydrochloride is added to 270 ml thionyl bromide, which has been cooled to 0C. The yellow-coloured solution is allowed to return to room temperature. Excess thionyl bromide is distillated for 45 minutes under reduced pressure. The remainder solidifies upon cooling. The yield of 4-bromomethyl imidazole hydrobromide salt is about 50%.

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; Stichting Biomaterials, Science Center, VU, “BSC-VU”; EP364016; (1990); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 38993-84-9,Some common heterocyclic compound, 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, molecular formula is C5H8N2O, 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.

DIAD (0. [0195 MOL)] was added dropwise at a temperature between 0 and [5°C] to a mixture of 4-hydroxybenzaldehyde (0.015 mol), [5-HYDROXYMETHYL-1-METHYL-1H-] imidazole (CA No: 38993-84-9) (0.018 mol) and [PPH3] (0.0225 mol) in THF (40ml) under [N2] flow. The mixture was stirred at room temperature overnight, then stirred for a week end, diluted in EtOAc, extracted with [HC1] 3N, washed with EtOAc, alkalinized with [K2CO3] and extracted with EtOAc. The organic layer was separated, dried [(MGS04),] filtered, and the solvent was evaporated. Yielding: 1.6g of intermediate 38 (49percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-1H-imidazol-5-yl)methanol, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/7498; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 33468-67-6 as follows. Recommanded Product: 33468-67-6

A solution of ethyl 2-bromopropionate (3.98 g, 22 mmol), 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole (3.00 g, 20 mmol), and K2CO3 (5.53 g, 40 mmol) in THF/DMF (2:1, 39 mL) was allowed to stir at 45 C. for 16 h. The mixture was then concentrated in vacuo and diluted with EtOAc (70 mL). The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated in vacuo to give the product (5.3 g) as a colorless oil that was used without further purification.

According to the analysis of related databases, 33468-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Jaen, Juan C.; Li, Yandong; Powers, Jay P.; Malathong, Viengkham; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/179733; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, Recommanded Product: 3012-80-4

To a stirred suspension of 1-METHYL-1H-BENZOIMIDAZOLE-2-CARBALDEHYDE (980mg, 6. 61mmol) in H2O (10ML) was added a solution of Sodium Acetate (3. 25g, 39. 68MMOL) and Hydroxylamine hydrochloride (1. 38g, 19. 84MMOL) in 10ml of H2O. The reaction was stirred at rt for 2hr and the thick precipitate was collected by filtration, washed with water and dried under vacuum to give 1. 02g (94%) of a white solid.’H NMR (DMSO-d6) 5 12.06 (1 H, s), 8.28 (1 H, s), 7.65 (1 H, d, J = 7.5 HZ), 7.60 (1 H, d, J = 6.8Hz), 7.32 (1 H, t, J = 7.2 Hz), 7.23 (1 H, t, J = 6.8 Hz), 4.00 (3H, s). Anal. Calcd for C9H9N30 : C, 61.70 ; H, 5.18 ; N, 23.99. Found: C, 61.80 ; H, 5.23 ; N, 23.98.

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; PFIZER INC.; WO2004/56806; (2004); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., Quality Control of Di(1H-imidazol-1-yl)methanimine

Example 14: r4-(5-Amino- Pl .3.41 oxadiazol-2-yl)-pyridin-3-yll-(2,4-dibromo- phenvP-amine; To a solution of 3-(2,4-Dibromo-phenylamino)-isonicotinic acid hydrazide (200mg, 0.52 mmol) in DMSO (2ml_) C- (Di-imidazol-i-yl)-methyleneamine (167mg, 1.04 mmol) was added. The reaction mixture was stirred at RT under Argon overnight, then poured into water. A solid precipitated out, which was filtered, and washed with methanol to afford the desired product (100mg). LC/MS (Method A) [5.23min; 412(M+1)].

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; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem