Tag: M.W=200-300

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. 14813-85-5, name is 1-Phenyl-1H-benzo[d]imidazol-2(3H)-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C13H10N2O

a.) 21.0 g (100 mmol) 3-phenyl-1H-benzimidazol-2-one and 24.2 g (110 mmol) 4-bromo-2- fluoro-1-nitro-benzene, 27.6 g (200 mmol) potassium carbonate in DMF is stirred at 100 C for 20 h. The reaction mixture is poured in water and the water phase is extracted with (0803) dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is removed in vacuum. Yield 23 g (56 %) 1H NMR (400 MHz, CDCl3): ^ = 8.11 (d, 1H), 7.92 (d, 1H), 7,79 (dd, 1H), 7.55.7.61 (m, 4H), 7.44-7.48 (m, 1H), 7.15-7.21 (m, 3H), 7.00-7.05 (m, 1H).

According to the analysis of related databases, 14813-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (320 pag.)WO2017/56053; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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 28890-99-5, Application In Synthesis of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

Example 6 a) 20.0 g (78.8 mmol) 1,3-dibromo-5-fluoro-benzene, 16.3 g (78.8 mmol) 6H-benzimidazolo[1,2-a]benzimidazole and 43.5 g (0.315 mmol) potassium carbonate in 200 ml DMF are stirred for 17 h at 170 C. The reaction mixture is filtered hot and the precipitate from the mother liquor is filtered after cooling. The product is washed with water and ethanol and decocted with diethyl ether and ethanol. Yield 21.2 g (61%).1H NMR (400 MHz, THF-d8): delta 8.21-8.26 (m, 4H), 7.98-7.8.00 (m, 1H), 7.68-7.73 (m, 2H), 7.31-7.49 (m, 4H).

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; BASF SE; US2012/241681; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-13-3, 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 641571-13-3 as follows.

General procedure: A mixture of compound 6a (20.0 mg, 0.06 mmol), 3-trifluoromethyl-benzoic acid (23.11 mg, 0.12 mmol), HOBt (18.1 mg, 0.13 mmol), and EDCI (29.1 mg, 0.15 mmol) in dry DMF (1.0 mL) was cooled to 0 C under nitrogen atmosphere. To the reaction mixture, triethylamine (0.002 mL, 0.015 mmol) was added at 0 C. The mixture was then stirred at 80 C for 12 h. The reaction mixture was cooled and then partitioned between water (5 mL) and ethyl acetate (5 mL) and the organic layer was separated. The aqueous layer was then extracted with ethyl acetate (3 × 3 mL) and the combined organic extracts were washed with brine and dried over anhydrous Na2SO4. After evaporation of the organic solvent, the residue was purified by column chromatography (silica gel, hexane-ethyl acetate 3:1 v/v then switching to hexane-ethyl acetate 1:1 v/v) to yield compound 9a (5.0 mg, 16.4%).

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; El-Gamal, Mohammed I.; Jung, Myung-Ho; Lee, Woong San; Sim, Taebo; Yoo, Kyung Ho; Oh, Chang-Hyun; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3218 – 3226;,
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Imidazole | C3H4N2 – PubChem

Reference of 1231930-33-8,Some common heterocyclic compound, 1231930-33-8, name is 6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzo[d]imidazole, molecular formula is C11H12BrFN2, 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.

6-Bromo-4-fluoro-1-isopropyl-2-methyl-1H-benzimidazole (200 mg, 0.73765 mmol) (compound represented by formula 1-a), bis(pinacolato)diboron (280 mg, 1.1 mmol), tricyclohexylphosphine (37 mg, 0.1320 mmol), potassium acetate (218 mg, 2.221 mmol) and palladium acetate (19 mg, 0.1148 mmol) were added to dimethyl sulfoxide (2 mL), and the mixture was stirred under nitrogen atmosphere at 90 C. for 2 hours. After cooling to room temperature, the reaction solution was diluted with 10 mL ethyl acetate and filtered. The filtrate was washed with saturated brine, dried over anhydrous sodium sulfate. The organic layer was concentrated and purified by silica gel column chromatography (ethyl acetate/n-hexane 0 to 50%) to give compound 4-fluoro-1-isopropyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzimidazole represented by formula 1-b (180 mg, 0.5657 mmol). LC-MS: m/z: (M+H)+=319.2.

The synthetic route of 1231930-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Pharmaceuticals Holding Co., Ltd.; XIA, Guangxin; WANG, Qian; SHI, Chen; ZHAI, Xiong; GE, Hui; LIAO, Xuemei; MAO, Yu; XIANG, Zhixiong; HAN, Yanan; HUO, Guoyong; LIU, Yanjun; (202 pag.)US2019/10153; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 95470-42-1, 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 95470-42-1 as follows.

B. To a stirred suspension of ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (0.90 g, 3.86 mmol) and potassium carbonate (1.07 g, 7.74 mmol) in N,N-dimethylformamide (15 mL) under nitrogen atmosphere was added iodomethane (0.73 mL, 11.6 mmol). The reaction mixture was stirred for 1.5 h, and diluted with ethyl acetate (75 mL). The organic layer was washed with water (25 mL) and brine (25 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 10-60percent ethyl acetate in hexanes to afford the title compounds. First fraction: ethyl 2-bromo-1,4-dimethyl-1H-imidazole-5-carboxylate (0.61 g, 64percent): 1H NMR (300 MHz, CDCl3) delta 4.33 (q, J=7.1 Hz, 2H), 3.86 (s, 3H), 2.46 (s, 3H), 1.38 (t, J=7.1 Hz, 3H); MS (ES+) m/z 247.1 (M+1). Second fraction: ethyl 2-bromo-1,5-dimethyl-1H-imidazole-4-carboxylate (0.30 g, 32percent); 1H NMR (300 MHz, CDCl3) delta 4.35 (q, J=7.1 Hz, 2H), 3.54 (s, 3H), 2.56 (s, 3H), 1.38 (t, J=7.1 Hz, 3H); MS (ES+) m/z 247.1 (M+1).

According to the analysis of related databases, 95470-42-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 95470-42-1, name is Ethyl 2-bromo-4-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. HPLC of Formula: C7H9BrN2O2

Example 12.2 Synthesis of Ethyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methyl-1H-imidazole-5-carboxylate Following the procedure as described in Example 12, making variations only as required to use 4-(benzyloxy)pyridin-2(1H)-one in place of 4-phenylpyridin-2-ol to react with ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate in place of ethyl 2-bromo-4-methylthiazole-5-carboxylate at 130° C. for 54 hours, the title compound was obtained as a colorless solid in 26percent yield: mp 135-136° C.; 1H NMR (300 MHz, CDCl3) delta 12.01 (s, 1H), 8.60-8.50 (m, 1H), 7.44-7.36 (m, 5H), 6.21 (dd, J=8.0, 2.6 Hz, 1H), 6.04 (d, J=2.6 Hz, 1H), 5.06 (s, 2H), 4.44-4.29 (m, 2H), 2.59-2.51 (m, 3H), 1.44-1.34 (m, 3H); MS (ES+) m/z 354.2 (M+1).

The synthetic route of Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dales, Natalie; Fonarev, Julia; Fu, Jianmin; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Pokrovskaia, Natalia; Raina, Vandna; Sun, Shaoyi; Zhang, Zaihui; US2009/156615; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-70-0, The chemical industry reduces the impact on the environment during synthesis 870837-70-0, name is 4-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, I believe this compound will play a more active role in future production and life.

l-(4-Ethynyl-2-methoxyphenyl)-l//-imidazole.A mixture of 4-fiuoro-3-methoxybenzaldehyde (1.0 g, 6.5 mmol) in 20 mL of DMF was treated with 4-methylimidazole (1.0 g, 15 mmol) and warmed to 130 C. Stirred overnight. Diluted with EtOAc, washed with sat’d NaHCO3, dried (Na2SO4), concentrated. Dissolved in 20 mL of MeOH, treated with K2CO3 (2.0 g, 14 mmol) and dimethyl (l-diazo-2-oxopropyl)phosphonate (1.5 g, 7.8 mmol) and stirred overnight. Diluted with DCM and washed with water. Dried (Na2SO4), cone. Chromatography on silica (0-20% MeOH/DCM) gave the desired alkyne:1H NMR (600 MHz, CDCl3) delta7.79 (s, 1 H), 7.18 (t, J= 1.2 Hz, 1 H), 7.16 (d, J= 1.8 Hz, 1 H), 7.15 (m, 2 H), 7.13 (d, J= 1.5 Hz, 1 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-(1H-Imidazol-1-yl)-3-methoxybenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/156580; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 28890-99-5, 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 28890-99-5 as follows.

Example 3 3.30 g (10 mmol) 1,3-diiodobenzene, 13.0 g (40.0 mmol) caesium carbonate, 1.90 g (1.00 mmol) copper(I) iodide and 2.30 g (20.0 mmol) L-proline are added to 4.56 g (22.0 mmol) mmol) 5H-benzimidazo[1,2-a]benzimidazole in 100 ml dimethylsulfoxide (DMSO) under nitrogen. The reaction mixture is stirred for 5 h at 100 C. The reaction mixture is poured into water and the product is filtered off. The product is two times crystallized form toluene. Yield 1.6 g (48%). MS (APCI(pos): m/z=489 (M+1).1H NMR (400 MHz, THF-d8): delta 8.79 (s, 1H), 8.22 (d, J=8.4 Hz, 2H), 8.15-8.18 (m, 2H), 8.00-8.06 (m, 4H), 7.88 (t, J=8.1 Hz, 1H) 7.71 (d, J=7.9 Hz, 2H), 7.41-7.49 (m, 4H), 7.25-7.34 (m, 4H).

According to the analysis of related databases, 28890-99-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2012/241681; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3543-73-5, The chemical industry reduces the impact on the environment during synthesis 3543-73-5, name is Ethyl 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, I believe this compound will play a more active role in future production and life.

Method B: To a 500 mL three-neck glass flask equipped with a heating mantle, thermocouple, condenser, nitrogen inlet/outlet, and overhead stirrer was charged 4-(5-amino-l- methyl-lH-benimidazol-2-yl)-butyric acid ethyl ester (6.4g, 1.0 eq.), chloroacetic acid (42.5 g), and tetrahydrofuran (THF, 13 mL). The resulting mixture was stirred for 1.5 hours in a water bath at room temperature. Borane-THF (150 mL) was added over 20 minutes. Once the charge was complete, the reaction mixture was heated to 55-58 C and stirred for 1.5 hours. In-process analysis by HPLC showed 94A% of the desired product. The reaction was cooled to room temperature and telescoped to the next step of hydrolysis to generate bendamustine.

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 4-(5-amino-1-methyl-1H-benzo[d]imidazol-2-yl)butanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPHALON, INC.; BAKALE, Roger, P.; BROWN, Peter, D.; CHEN, Jian; DRAGER, Anthony, S.; LABELL, Rachel, Y.; MCKEAN, Robert, E.; PATEL, Piyush, R.; ROEMMELE, Renee, C.; WO2014/75035; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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. Product Details of 144689-93-0

Example 3; Preparation of olmesartan medoxomilTo dimethyl acetamide (800 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium carbonate (200 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (300 gms) at 45-50C. The contents were stirred for 8-10 hours at 45-50C. The insolubles were filtered. The contents were cooled to 5-100C. Potassium tertiary butoxide (100 gms) was charged at a temperature below 45C. The reaction was maintained at 40-450C for 3 hrs. To this was slowly added 5-methyl-2-oxo-1 ,3-dioxane-4-yl) methyl chloride at 40-450C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganics. The reaction mass was charcoalized using charcoal (10 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500 ml), neutralized with base and extracted in dichloromethane (500 ml).The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (250 ml) to give 55 gms of the title compound. Chromatogrphic purity- > 99%

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

Reference:
Patent; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem