Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

(2) Synthesis of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid Ethyl diethylphosphonoacetate (5.7 g) and lithium hydroxide monohydrate (1.3 g) were sequentially added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5.0 g) in THF (20 mL) and ethanol (5 mL), and the reaction solution was stirred at room temperature for nine hours. A 2 N sodium hydroxide solution (20 mL) was added to the reaction solution, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was cooled to 0 C., and 2 N hydrochloric acid (20 mL) was added to the reaction solution. The resulting precipitate was collected by filtration. The resulting precipitate washed with water and ethyl acetate to obtain 5.1 g of the title compound. The property values of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 2.15 (s, 3H), 3.88 (s, 3H), 6.66 (d, J=16.0 Hz, 1H), 7.16 (s, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.39 (d, J=8.0 Hz, 1H), 7.56 (s, 1H), 7.60 (d, J=16.0 Hz, 1H), 7.81 (s, 1H).

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; Eisai R&D Management Co., Ltd.; US2007/219181; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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. Product Details of 1450-93-7

1.1. 7-(pyrimidin-4-yl)-1 H-imidazo[1,2-a]pyrimidin-5-one A mixture containing 2.9g (15 mmol) of 3-oxo-3-(pyrimidin-4-yl)-propionic acid ethyl ester (prepared by analogy to the method described in patent DE 2705582), 2g (15 mmol) of 2-aminoimidazole hemisulfate and 1.2g (15 mmol) of ammonium acetate was heated at 140ØC during 18 h. The cooled mixture was treated with 30ml of acetonitrile and filtered and the precipitate was added to water and heated at reflux temperature for 30 min. The resulting solution was cooled and the precipitate recovered by filtration. The crude product thus obtained was recrystallised from ethanol to give 1.75g of pure product as a gray solid. Mp: 345-346ØC

The synthetic route of 1H-imidazol-2-amine sulfate(2:1) has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION; EP1340759; (2003); 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

Step B:; To a solution of 77.1 b (300 mg, 1.01 mmol) in THF (5 ml) was added ‘PrMgCI. LiCI (1 M in THF, 1.3 ml, 1.3 mmol) and stirred at room temperature for 10 min, followed with addition of 77.1c (216 mg, 1.01 mmol). The resulting mixture was stirred overnight, then quenched with saturated aqueous NH4CI, extracted with EtOAc (3 X). The combination of organic layers was washed with brine, dried (Na2SO4), concentrated and purified by flash chromatography to afford product 77.1 as colorless oil (210 mg, 48%). 1H NMR (CDCI3, ppm) 7.39-7.36 (m, 1 H), 7.31-7.25 (m, 3H), 7.20- 7.10 (m, 2H), 7.09-7.02 (m, 4H), 6.44-6.35 (m, 1 H), 6.28-6.20 (m, 1 H), 5.85 (d, 1 H), 3.89 (d, 3H), 2.47 (s, 3H), 1.75-1.70 (m, 3H); MS (ES-LCMS, M+1 ) 434.2. Retention time: 2.55 min.

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/32277; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10351-75-4,Some common heterocyclic compound, 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, molecular formula is C9H6N2O4, 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 reaction mixture of MnCl2 (0.2 mmol, 25.2 mg), H3bidc(0.1 mmol, 20.6 mg), and phen (0.1 mmol, 19.8 mg), H2O(4mL) and DMF (4 mL) was stirred for half an hour, thentransferred and sealed in a 10 mL glassflask. The system washeated in an oven at 85C for 24 hours and cooled to roomtemperature. Accordingly colourless block crystals were isolated by filtering, washed with distilled water and dried at inair. The yield of colorless crystalline product was 58% (basedon Mn). Anal. Calcd for C9H6N2O5Mn: C, 38.98; H, 2.17;N, 10.10%. Found: C, 38.85; H, 2.04; N, 10.02%. IR (KBrcm1): 3398(s), 3119(s), 1548(s), 1412(s), 1270(w), 1176(s),1122(s), 959(m), 876(m), 804(m), 629(w), 589(w), 429(m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, its application will become more common.

Reference:
Article; Zhang, Huijie; Zhou, Guangpeng; Fan, Ruiqing; Wang, Xinming; Yang, Yulin; Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry; vol. 46; 8; (2016); p. 1224 – 1235;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10351-75-4,Some common heterocyclic compound, 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, molecular formula is C9H6N2O4, 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.

Europium oxide (0.1 mmol, 35.2 mg),H3bidc (41.2 mg, 0.2 mmol) and a solution (1 ml) of oxalic acid(0.1 M) were dissolved in water (10 ml) at room temperature.After continuous stirring for 10 min, the mixture was sealed ina Teflon-lined stainless steel vessel (23 ml), heated at 180 C for 3 d under autogenous pressure and cooled slowly to room temperature. Yellow block-shaped crystals of 1 were harvestedin a yield of 80% (based on Eu). Elemental analysis (%)calculated for C10H8EuN2O8: C 27.54, H 1.85, N 6.42; found: C27.32, H 1.90, N 6.51. IR (KBr, cm-1): 3130 (m, br), 1680 (s),1620 (m), 1575 (s), 1410 (w), 1380 (m), 1209 (m), 1102 (s), 1110(vs), 1000 (m), 890 (s), 813 (m), 650 (w), 580 (w).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, its application will become more common.

Reference:
Article; Wenxu, Zheng; Wu, Kechen; Acta Crystallographica Section C: Structural Chemistry; vol. 76; (2020); p. 186 – 192;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 84946-20-3, 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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, 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.

EXAMPLE 43 Norastemizole. To a 25 mL 3-neck flask equipped with a thermometer, ref lux consenser and stir bar were added, under a nitrogen atmosphere, 822 mg (4.8 mmol) of Compound XVI, obtained according to the procedure of Example 6, and 0.93 mL (8.0 mmol) of lutidine. The mixture was heated to 120 C., whereupon a solution of 1.04 g (4 mmol., 1 eq.) of Compound X (Aldrich Chemical Co., Milwaukee, Wis.), 8 mmol of tetrabutylammonium fluoride (obtained from its 1.0M THF solution by distillation under vacuum with anhydrous toluene) and 4 mL of N-methylpyrrolidinone was added slowly over 2 h. The reaction mixture was allowed to stir at 120 C. for 2 h. High-performance liquid chromatography revealed >95% coversion to Compound XVIII. The reaction mixture was allowed to cool to ambient temperature, and slowly poured into a solution of 5% aqueous NaOH while stirring. The resulting suspension was allowed to stir at 0-10 C. for 30 minutes, and the resulting solid product was collected by vacuum filtration, washed with water (3*5 mL), and air dried for 30 minutes under vacuum to afford a crude mixture of Compound XVIII and 6% (HPLC) of migration product Compound XIX. NMR data for Compound XVIII: 1 H NMR (300 MHz, DMSO-d6) delta7.30-7.02 (6H, m two groups), 6.95 (1H, pseudo t, J=7.8, 2.3 Hz), 6.85 (1H, pseudo t, J=7.8, 2.3 Hz), 5.35 (2H, s), 4.33 (1H, pseudo d), 4.02 (1H, m), 3.83 (1H, pseudo d), 3.17 (1H, pseudo t), 2.75 (1H, pseudo t), 2.02 (3H, s), 2.0 (2H, m overlapped), 1.45 (2H, m); 13 C NMR (75 MHz, DMSO-d6) delta168.0, 163.0 and 159.7 (13 C-19 F coupling), 153.9, 142.8, 134.3, 133.5, 129.1, 129.0, 128.2, 120.5, 118.4, 115.5, 115.2, 107.9, 44.8, 43.7, 32.3, 31.5, 21.4. It is to be noted that under the same reaction conditions as above, but without the use of tetrabutylammonium fluoride, only 4.9% conversion (high-performance liquid chromatography) to Compound XVIII was achieved after 3 h at 120 C. In addition, without the use of tetrabutylammonium fluoride, the ratio of Compound XVIII:Compound XIX was 4:1. The mixture of Compound XVIII obtained above was placed in a 50 mL, 3-neck flask equipped with a thermometer, reflux condenser and stir bar. 5 mL of 6N hydrochloric were added, and the resulting mixture was heated to 110 C. and allowed to stir at that temperature for 5 h. After the reaction was complete (>98% conversion to norastemizole as shown by high-performance liquid chromatography), the reaction mixture was allowed to cool to room temperature, and 10 mL of toluene and 10 mL of water were added, with stirring.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Sepracor Inc.; US5817823; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 621-72-7, name is 2-Benzyl-1H-benzo[d]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 621-72-7, Recommanded Product: 621-72-7

To the reaction vessel was added 8.2 g of dibazole,63 g of 10 wt% hydrochloric acid solution and 1.2 g of activated carbon,Air was introduced into the reaction vessel while stirring, and the temperature was raised to 95 C.The reaction was stirred for 10 hours while the reaction was completed, and the air was stopped.Drop to 15 C, filter, and evaporate the filtrate under reduced pressure to give 8.5 g of crude material;The crude product was mixed with 70 g of anhydrous methanol and stirred and dissolved at 55 C.The mixture was filtered while hot, and the filtrate was stirred at 0 C for 3 hours, and filtered.Drying, 7.8 g of diazol oxidized impurity reference substance was obtained, and the yield was 89.3%.The purity was determined by HPLC to be 99.95%.

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, 2-Benzyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wuhan Xian Lu Pharmaceutical Technology Co., Ltd.; Huang Li; Ning Fan; Wu Bo; Wang Ge; Xie Shuwei; Chen Weijiang; (6 pag.)CN108863946; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 641571-11-1, A common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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.

A solution of potassium t-butoxide (11 mL of 1M solution, 5.5 equiv.) in THF was slowly (10 min) added to compound 3b (0.77 g, 2.0 mmol) and 1-(3-amino-5-trifluoromethylphenyl)-4-methyl-1Himidazole (0.45 g, 2.0 mmol) dissolved in THF (30 mL) at -15 to -10 C under an argon atmosphere. The dark red solution was stirred at room temperature for 3.5 h and then cooled to 0 C and treated with saturated NaCl aqueous solution (25 mL). The organic layer was separated; the aqueous one was extracted with EtOAc (2×15 mL). Combined organic extracts were dried (Na2SO4) and evaporated. The yellow solid residue was treated with toluene (5-10 mL) and filtered off to obtain nilotinib trifluoromethyl derivative 7 (0.8 g, 67%) as yellow solid; m.p. 269-271 C (EtOH); 1H NMR: delta 2.14 (3H, s, CH3), 2.32 (3H, s, CH3), 7.44 (1H, s, 5-H imidazole), 7.46 (1H, d, J = 8.1 Hz, 5-H), 7.50 (1H, dd, J = 8.0, 4.8 Hz, 5-H Py), 7.69 (1H, s, 2-H imidazole), 7.79 (1H, dd, J = 8.1, 1.7 Hz, 6-H), 7.88 (1H, s, Pm), 8.11 (1H, s, 2-H Ar), 8.16 (1H, d, J= 1.7 Hz, 2-H), 8.20 (1H, s) and 8.25 (1H, s) 4,6-H Ar, 8.48 (1H, dt, J= 8.0, 1.7 Hz, 4-H Py), 8.68 (1H, dd, J= 4.8, 1.7 Hz, 6-H Py), 9.29 (1H, d, J= 1.7 Hz, 2-H Py), 9.83 (1H, s, NH), 10.57 (1H, s, NH). 13C NMR: delta 13.5 (CH3), 18.2 (CH3), 103.2 (q, J= 3 Hz, C-5 Pm), 111.6 (q, J= 4 Hz, C-6 Ar), 114.2, 114.3 (q, J= 4 Hz, C-4 Ar), 115.0 (C-2 Ar), 120.7 (q, J= 274 Hz, CF3), 123.6 (q, J= 271 Hz, CF3), 123.8 (C-5 Py), 124.5, 124.8, 130.7, 130.8 (q, J= 32 Hz, C-CF3), 131.2, 131.9, 134.8 and 134.9 (C-4 Py, C-3), 137.3, 137.7, 137.9, 138.9, 141.3, 148.5 (C-6 Py), 152.2 (C-2 Py), 156.5 (q, J= 35 Hz, C-CF3Pm), 161.1 (C-4 Pm), 165.1 (C=O), 165.4 (C-2 Pm). Anal. calcd for C29H21N7F6O: C, 58.29; H, 3.54; N, 16.41; found: C, 58.30; H, 3.65; N, 16.22%.

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Terentjeva; Muceniece; Lusis; Journal of Chemical Research; vol. 39; 4; (2015); p. 223 – 225;,
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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(1H-Benzo[d]imidazol-2-yl)aniline

Example 37: Preparation OF 2-BENZO L, 3] DIOXOL-5-VL-N- [3- (LH-BENZIMIDAZOL-2-YL)- PHENYLL-ACETAMIDE (Compound M To a 5.0 ml methylene chloride solution of (3,4-methylene-dioxy) phenyl acetic acid (182. 9 mg, 1.0 mmol) was added methylene chloride oxalyl chloride solution (2 M, 0.60 ml, 1.2 mmol). Five drops of DMF was added with stirring at ambient temperature. Methylene chloride and other volatile materials were removed by reduced pressure after it was stirred at ambient temperature for 3.0 h. To the residue was added DMAP (10 MG), 4-(1H-benzimidazol-2-yl)-phenylamine (83 mg, 0.40 mmol) and pyridine (2.0 ml). The mixture was stirred at 60 C for 20 hrs. Water (20 ml) was added. The solid formed was collected and was washed with aq. NAOH (3 N, 2x 10 ml), water (10 ml), aq. HCl (2 N, 3 x 10 ml), water (2 x 5 ml), ether (2 x 5 ml). An off-white compound (12 mg, 8%) was obtained. MS M/Z = 372.05 (M+H) ; IH NMR delta 10.56 (s, 1 H), 8.15 (d, J=8. 7 Hz, 2 H), 7. 87 (d, J=8. 7 Hz, 2 H), 7.72 (m, 3 H), 7.42 (m, 2 H), 6.94-6. 80 (m, 3 H), 6.00 (s, 2 H), 3.63 (s, 2H).

According to the analysis of related databases, 2963-77-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IMCLONE SYSTEMS INCORPORATED; WO2005/30206; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 540516-28-7, name is 2-(Hydroxymethyl)-5-bromobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Hydroxymethyl)-5-bromobenzimidazole

Synthesis of 5-bromo-1H-benzimidazole-2-carboxylic acid hydrochloride 44 was prepared using 5-bromo-1H-benzimidazole-2-yl)-methanol 28 (0.23 g, 1.0 mmol) dissolved in acetone (10 mL) and potassium permanganate (0379, 2.4 mmol) dissolve in water (10 mL). The crude product was recrystallised from water. 5-Bromo-1H-benzimidazole-2-carboxylic acid in Yield 37% was recovered as a creamy white powder.

The synthetic route of 540516-28-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem