Tag: M.W=100-200

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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, A new synthetic method of this compound is introduced below., Formula: C4H6N4O2

In a 1,000-liter reactor was charged 320 kg of water, Heated to reflux, 71 kg of glycoluril and 58 kg of 50% glyoxal were successively added, Stirring to clear, In the refluxing state, 500 L of a sodium hydroxide solution (8 mol / l) was rapidly added dropwise, After completion of the dropwise addition, The refluxing reaction was continued for 8 hours. Close the heating,When the temperature naturally cool to room temperature,45 kg of chlorine gas was introduced into the reaction system,After completion of the reaction,Concentrated hydrochloric acid was added to adjust the pH to 1,Stirring was reduced to room temperature,After 2 hours,Obtain crude orotic acid.In the 2000-liter reactor, the crude orotate was added and 600 kg of water was added. After boiling, add the concentrated ammonia to dissolve, then add 5 mol / L sulfuric acid to adjust the pH to weak acidity, add activated carbon to boil for 30 minutes, filter it hot, adjust the pH to 1 with concentrated sulfuric acid, Dry, get whey acid finished 25.7 kg, yield 33%, purity 99.9%.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Baishixing Science and Technology Industry Co., Ltd.; Shi, Changqing; (6 pag.)CN106187918; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 106429-59-8,Some common heterocyclic compound, 106429-59-8, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, molecular formula is C8H6N2O2, 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 mixture of intermediate 62 (120 mg, 0.32 mmol), 2-oxo-2,3-dihydro-1Hbenzo[d]imidazole-S-carbaldehyde (CAS: 106429-59-8) (104 mg, 0.64 mmol) and TiG-PrO)s (92 mg, 0.32 mmol) in DCE/DMSO(6 mL/2 mL) at 0 C was added NaBH(OAc); (205 mg, 0.97 mmol) in portions. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with aq. NaHCOsand the resultant was extracted with DCM. The combined organic extracts were washed with brine, dried over anhydrous Na2SQOuq,filtered and concentrated. The residue was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19*150 mm 10 um, Mobile Phase A: H,O (0.1% TFA), B: ACN) to give Compound 117 (22 mg TFA salt, yield: 13%) as a 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-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
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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. 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41716-18-1

To a solution of 1-methyl-1Himidazole-4-carboxylic acid (0.50 g, 4.0 mmol), 1-hydroxybenztriazole monohydrate (0.74 g, 4.8 mmol), and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) in acetonitrile (10 mL) was added a solution of 3-(trifluoromethoxy) benzylamine 8(0.84 g, 4.4 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for overnight. The reaction mixture was concentrated in vacuo, and saturated aqueous NaHCO3solution was added to the residue. After extraction with ethyl acetate, the organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (0?10percent MeOH in CHCl3) to obtain 9(1.18 g, 98percent) as a colorless powder.1H-NMR (600 MHz, CDCl3) delta: 3.73 (3 H, s), 4.62 (2 H, d, J=6.0 Hz), 7.08?7.13 (1 H, m), 7.18 (1 H, s), 7.26?7.29 (1 H, m), 7.31?7.37 (2 H, m), 7.44?7.51 (1 H, m), 7.55 (1 H, d, J=1.4 Hz); MS ESI: m/z300 [M+H]+.

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 41716-18-1.

Reference:
Article; Yamamoto, Shuji; Ohta, Hiroshi; Abe, Kumi; Kambe, Daiji; Tsukiyama, Naohiro; Kawakita, Yasunori; Moriya, Minoru; Yasuhara, Akito; Chemical and Pharmaceutical Bulletin; vol. 64; 11; (2016); p. 1630 – 1640;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-nitro-1H- imidazole (500 mg, 4.42 mmol) in DMSO (3 mL) was added but-3-en-2-one (465 mg, 6.63 mmol) followed by DMAP (32.4 mg, 0.265 mmol). The mixture was stirred at 70 C for 1.5 h. Water was added and extracted with EtOAc (3 x 50 mL). The organic layer was dried over Na2SO4 and concentrated to give 4-(4-nitro-1H-imidazol-1-yl)butan-2-one (420 mg, 2.293 mmol, 52 % yield). (2354) MS ESI m/z 184.0 (M+H)+ (2355) 1H NMR (499 MHz, CDCl3) delta 7.82 (d, J=1.5 Hz, 1H), 7.50 (d, J=1.4 Hz, 1H), 4.35 – 4.31 (m, 2H), 3.01 (t, J=6.0 Hz, 2H), 2.23 (s, 3H).

The synthetic route of 5-Nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WATTERSON, Scott Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; DZIERBA, Carolyn Diane; GONG, Hua; GUERNON, Jason M.; GUO, Junqing; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; VENABLES, Brian Lee; WEIGELT, Carolyn A.; WU, Yong-Jin; ZHENG, Zhizhen Barbara; SIT, Sing-Yuen; CHEN, Jie; (810 pag.)WO2019/147782; (2019); 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. 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39021-62-0

n-BuLi (2.5 M in hexanes, 0.52 mL, 1.3 mmol) was added dropwise to a solution of 6-bromo-2,4-dichloro-3-phenylquinoline (353 mg, 1 mmol, Intermediate 1: step c) in dry THF (10 mL) in a 100 mL three necked round bottomed flask at -78 C. under N2. Stirring was continued for 30 minutes then a solution of 1-methyl-1H-imidazole-5-carbaldehyde (110 mg, 1 mmol) in dry THF (10 mL) was added at -78 C. The cooling bath was removed and the mixture was gradually warmed up to room temperature and stirred for 2 hours. The mixture was quenched by adding H2O (10 mL) and then extracted with CH2Cl2 (2*50 mL). The combined organic phase was dried over Na2SO4, concentrated to dryness and purified by prep-TLC (developed by CH3OH/CH2Cl2 1:5) to afford the title compound as a white solid. MS (ESI): 384.1 [M+H]+. 1H NMR (300 MHz, CD3OD) delta ppm 8.45 (s, 1H), 7.94 (dd, J=42.2, 8.0 Hz, 2H), 7.73-7.24 (m, 6H), 6.56 (s, 1H), 6.16 (s, 1H), 3.70 (s, 3H).

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 39021-62-0.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); 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. 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5BrN2

To a solution of 5-bromo-1-(triphenylmethyl)-1H-benzimidazole and 6-bromo-1-(triphenylmethyl)-1H-benzimidazole (1:1 mixture) (6.0 g, 13.7 mmol) in toluene (30 mL), was added tetrakis(triphenylphosphine) palladium(0) (0.8 g, 0.7 mmol), followed by a solution of sodium bicarbonate (2.9 g, 34.2 mmol) in water (15 mL). A solution of 3-formylphenylboronic acid (2.3 g, 15.0 mmol) in ethanol (8 mL) was then added and the reaction was heated at reflux overnight. After cooling, the bulk of the solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and water. The organics were washed with brine, dried (Na2SO4), and concentrated in vacuo. Chromatography of the residue on silica gel (35-50% EtOAc/hexanes) provided the product as an inseparable mixture of trityl regioisomers, 3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]benzaldehyde and 3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]benzaldehyde. (M+1) 465.2 ES, 3.01 min and 3.05 min (LC-MS Method A).

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; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 10040-98-9, name is 4-Imidazol-1-yl-benzaldehyde, 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 10040-98-9, SDS of cas: 10040-98-9

A mixture of malonitrile (30.0 mg, 0.45 mmol) and 4-(1H-imidazol-1- yl)benzaldehyde (78.0 mg, 0.45 mmol) in anhydrous ethanol ( 4.0 mL) was charged with N- methylmorpholine (0.05 mL, 0.45 mmol) for 2 minutes. To the mixture was added 1-(4- fluorophenyl)-3-methyl-1H-pyrazol-5(4H)-one (90.0 mg, 0.45 mmol) in one portion at room temperature. The reaction mixture was stirred at room temperature for 48 hrs. The suspension was filtered under vacuum and off white solid was obtained. The solid was gently washed with hexanes (20 mL) and chilled ethanol (10 mL) and further dried under high vacuum to provide compound 44 as an off white solid (170 mg, 88%).1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.25 (s, 1H), 7.83-7.74 (m, 3H), 7.62 (d, J = 8.4 Hz, 2H), 7.40 (d, J = 8.4 Hz, 2H), 7.36-7.26 (m, 4H), 7.10 (s, 1H), 4.77 (s, 1H), 1.82 (s, 3H). MS (ESI): Calcd for C23H17FN6O: 412, found: 413 (M+H)+.

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-Imidazol-1-yl-benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANTBIOSCIENCE, INC.; TAO, Chunlin; YU, Chengzhi; POLAT, Tulay; YAN, Chao; RABIZADEH, Shahrooz; THEODORESCU, Daniel; (108 pag.)WO2016/205460; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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. COA of Formula: C5H6N2O2

Step 1 Preparation of 1-trityl-1H-imidazole-4-carboxylic acid methyl ester A solution of 1H-Imidazole-4-carboxylic acid methyl ester (1.0 g, 7.93 mmol) in N,N-dimethylformamide at 25 C. was treated with triethylamine (2.2 mL, 15.86 mmol) and triphenylmethylchloride (2.43 g, 8.72 mmol). The reaction was stirred at 25 C. for 8 h and then concentrated in vacuo. The residue was diluted with ethyl acetate and then washed with water, a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50:50 ethyl acetate/petroleum ether) afforded 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.88 g, 98.6%) as a white foam: 1H NMR (DMSO-d6, 300 MHz) delta7.56 (s, 1H), 7.47 (m, 10H), 7.09 (m, 6H), 3.69 (s, 3H).

The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dunten, Peter W.; Foley, Louise H.; Huby, Nicholas J.S.; Pietranico-Cole, Sherrie L.; Yun, Weiya; US2004/14766; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 4857-06-1, 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. 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-Chloro-1H-benzimidazole (7.5 g, 49 mmol) was dissolved in dimethylformamide (20 mL),and the reaction mixture was cooled to oo C. Sodium hydride ( 60% dispersion in mineral oil 2.16 g,5 5.4 mmol) was carefully added. The reaction mixture was stirred at ambient temperature for 1 hour,and after that iodomethane (8.37g, 59 mmol) was added. The reaction mixture was stirred at ambienttemperature overnight, and then water (200 mL) was added. The solid was collected by filtration toafford 5 g, 61% of the titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) o ppm 3.79(s, 3H), 7.21-7.33 (m, 2H), 7.58 (t, J=7.0 Hz, 2H).

The synthetic route of 2-Chloro-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; GOMTSIAN, Artour; DEKHTYAR, Tatyana; FRANK, Kristine E.; FRIEDMAN, Michael M.; JOSEPHSOHN, Nathan; MOLLA, M-Akhteruzz; VASUDEVAN, Anil; NG, Teresa; SHAFEEV, Mikhail; WO2014/5129; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 29043-48-9, 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. 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: First, a mixture of 4-nitrobenzene-1,2-diamine (1 g) and formic acid (0.74 mL) in 5 N HCl (70 mL) was stirred and heated to reflux for 24 h. The mixture was cooled to room temperature and neutralized by 10% NaOH, and precipitate was isolated, recrystallised from water and dried to produce 5-nitrobenzoimidazole (0.69 g) [37]. Next, 5-nitrobenzoimidazole (0.25 g) was dissolved in ethanol (20 mL). The solution was stirred and heated to reflux, and the palladium-on-charcoal catalyst (0.15 g) and hydrazine hydrate (1.6 mL) were added. Then the mixture was stirred for 4 h, and filtered in hot. The filtrate was evaporated, and the residue was recrystallised from ethanol to give rise to the precursor compound 5-aminobenzoimidazole (0.163 g). Finally, a mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (0.25 g), 5-aminobenzoimidazole (0.15 g) in isopropanol (25 mL) was stirred and heated to reflux for 4 h. The precipitate was filtered off, recrystallised from methanol and dried to afford 12 as yellow powder (0.32 g, yield 73%).

The chemical industry reduces the impact on the environment during synthesis 2-Methyl-1H-benzoimidazol-5-ylamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Lue, Shuang; Zheng, Wei; Ji, Liyun; Luo, Qun; Hao, Xiang; Li, Xianchan; Wang, Fuyi; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 84 – 94;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem