Tag: M.W=200-300

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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C9H6N2O4

A mixture containing Sm2O3 (0.2 mmol), MnSO4*H2O (0.3 mmol), H3bidc (0.6 mmol) and water (10 mL) was sealed in a Teflon-lined stainless steel vessel (23 mL), which was heated at 160 C for 4 days and then cooled to room temperature in 2 days. Colorless rhombic crystals of 1 were obtained and picked out, washed with distilled water and dried in air (Yield: 44.6% based on Sm). Elemental Anal. Calc. C18H24Sm2MnN4O24S2: C, 19.65; H, 2.20; N, 5.09. Found: C, 19.35; H, 2.04; N, 4.95%. IR (KBr, cm-1): 3448.78vs, 1637.12s, 1555.48m, 1504.31m, 1479.17w, 1418.99m,1384.33s, 1098.76m, 642.16m.

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:
Article; Sun, Ya-Guang; Zong, Wen-Hui; Xiong, Gang; Guo, Mei-Yan; Ding, Fu; Wang, Shu-Ju; You, Li-Xin; Ren, Bao-Yi; Xu, Zhen-He; Gao, En-Jun; Polyhedron; vol. 83; (2014); p. 68 – 76;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 15813-07-7, The chemical industry reduces the impact on the environment during synthesis 15813-07-7, name is 5-Iodo-4-methyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

Step B 1-Boc-4-iodo-5-methylimidazole A suspension of 4-iodo-5-methylimidazole (4.16 g, 20 mmol) and di-t-butyldicarbonate (5.24 g, 24 mmol) in methylene chloride (100 ml) containing triethylamine (4.0 ml, 28.7 mmol) was stirred at room temperature until homogeneity was achieved (2 h). The reaction mixture was then washed well with water, dried (Na2 SO4) and concentrated. The residue was chromatographed (5:1 hexane/ethyl acetate) to afford the title compound as a crystalline white solid. 1 H NMR (CDCl3) d 1.62 (s, 9 H), 2.43 (s, 3 H), 8.00 (s, 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, 5-Iodo-4-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5932606; (1999); A;,
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 870837-18-6 as follows. name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Compound B2 (R2 = H, 1.5 g, 5.6 mmol, synthesized as in Tett. 1987, 43, 5125) in 40 ml of anhydrous THF at 0 0C was treated with NaH (0.25 g, 5.9 mmol, 60% in mineral oil). After 20 min, B1 (R8 = H, R10 = 3-MeO-Phenyl, R9 = 4-(4- Methylimidazol-1-yl), 1.Og, 4.62 mmol) was added and the reaction warmed to ambient temperature. After 18 h, the reaction mixture was quenched with saturated aqueous NH4CI and extracted with EtOAc (2x). The combined organic layers washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (gradient 1? 10 % MeOH/CH2CI2) provided 1.2 g (81 %) of B3 (R8 = H, R2 = H, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol-1-yl)).

According to the analysis of related databases, 870837-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2009/20579; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

A three-necked 250 mL round bottom flask equipped with thermometer, condenser, and stir bar, was charged with toluene (75 mL), ethyl 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoate (3 g, 9.0 mmol, 1 eq.), and 5-(4-methyl)-1H-imidazol-1-yl)-3-(trifluoromethyl)benzenamine (2.82 g, 11.7 mmol, 1.3 eq.). The suspension was warmed up and 6.8 mL AlMe3 (2 M in toluene, 13.8 mmol, 1.5 eq.) was added. The entire mixture was then being refluxed for 5 hrs until the ester disappeared and the process was monitored by an HPLC. After the mixture was cooled down, excess trimethyl aluminum was quenched with aqueous sodium hydroxide. The product was isolated by filtration and dried under vacuum affording 4.32 g (91%) nilotinib with 99.3% purity (HPLC). Results of other examples with different ratio of starting material are listed in the Table 2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; FORMOSA LABORATORIES, INC.; Hung, Jui-Te; Chen, Wen-Chin; US9187452; (2015); B1;,
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 71759-88-1 as follows. Safety of 5-Iodo-1-methyl-1H-imidazole

In a 10 mL two-necked flask, 5-iodo-1-methyl-1H-imidazole (150 mg, 721 mumol, Eq: 1.00) was combined with DCM (3 ml) to give a colorless solution. Ethylmagnesium bromide (264 mul, 793 mumol, Eq: 1.1) was added at rt over 2 min (white precipitate). After stirring for 1 hr, the reaction mixture was cooled to 0 C., and a solution of 4-chlorobenzaldehyde (132 mg, 937 mumol, Eq: 1.3) in DCM (2 ml) was added dropwise, and the mixture was stirred at rt. TLC after 2 h indicated the absence of starting material. Work up: The reaction mixture was quenched with sat. NaHCO3 (10 mL) and extracted with AcOEt (2*20 mL). The organic layers were washed with H2O/NaCl sol., the organic layers were combined, dried over Na2SO4, and concentrated i. V. The product was precipitated from DCM, filtered and dried on h. V. MS (ESI): 223.1/225.0 [M+H]+.

According to the analysis of related databases, 71759-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HOFFMANN-LA ROCHE INC.; Aebi, Johannes; Amrein, Kurt; Hornsperger, Benoit; Kuhn, Bernd; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; US2014/128429; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 5395-50-6,Some common heterocyclic compound, 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C8H14N4O6, 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.

1 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (1.88 g, 7.2 mmol) in 1.5 ml of DMSO was dissolved. Then, 0.15 ml nitric acid (65%) and n-l3uOH (13.12 ml, 143 mmol) were added to the solution and the mixture was heated at 60 C. for 16 hours. After the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. After being dried by Na2504, the solvent was removed. The crude compound was purified by flash chromatography (Heptane/EtOAc). The product was obtained colorless viscous oil in 0.38 g, yield (11%) ?H NMR (600 MHz, DMSO-d6): oe (ppm) 5.52 (s, 2H), 4.73 (m, 8H), 3.35 (m, 8H), 1.46 (m, 8H), 1.29 (m, 8H), 0.85 (t, 12H)

The synthetic route of 5395-50-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-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 6154-30-9, SDS of cas: 6154-30-9

Reference example 2 Preparation of 2,5-dibromo-1-methoxymethyl-4-nitroimidazole Under an ice-cooling condition, sodium hydride (3.56 g) was added to a N,N-dimethylformamide (100 ml) solution of 2,5-dibromo-4-nitroimidazole (20.08 g). 10 minutes later, being added dropwise chloromethylmethyl ether (6.75 ml) thereto at 10 to 15C, then the reaction mixture was turned back to a room temperature. After being stirred this reaction mixture for 5 hours, under an ice-cooling condition, sodium hydride (0.30 g) and chloromethylmethyl ether (0.56 ml) were added, further stirred at a room temperature for 1 hour. Then the reaction mixture was ice-cooled, water was added and extracted with ethyl acetate. The organic layer was washed with an aqueous solution being saturated with sodium chloride, dried over anhydrous sodium sulfate, then concentrated under a reduced pressure. Thus obtained crude crystals were washed with diisopropyl ether, and dried at 50C for 24 hours, there was obtained 2,5-dibromo-1-methoxymethyl-4-nitroimidazole (19.68 g, yield: 84.3%) as yellow powder product.

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, 2,5-Dibromo-4-nitro-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Company, Limited; EP1553088; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 95470-42-1, name is Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, 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 95470-42-1, Safety of Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate

Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate (2.75 g, 11.8 mmol) was dissolved in DMF (20 mL), potassiumcarbonate (3.26 g, 23.6 mmol) and 2,5-dichloronbenzyl bromide (3.4 g, 14.2 mmol) were added thereto, and thereaction mixture was stirred at 90°C for 3 hours. Water (50 mL) was added after the reaction was complete, andthe reaction mixture was extracted twice with ethyl acetate (50 mL). After washing with a saturated aqueous sodiumchloride solution, the organic phase was dried over sodium sulfate. After concentration under reduced pressure,the residue was purified by silica gel column chromatography to obtain ethyl 2-bromo-1-(2,5-dichlorobenzyl)-4-methyl-1H-imidazole-5-carboxylate (1.72 g) : 1H-NMR (CDCl3) delta: 7.34 (1H, d, J=8.8 Hz), 7.20 (1H, dd, J=8.8, 2.4Hz), 6.40 (1H, d, J=2.4 Hz), 5.60 (2H, s), 4.25 (2H, q, J=7.2 Hz), 2.56 (3H, s), 1.27 (3H, t, J=7.1 Hz); ESI-MS m/z=391(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-bromo-4-methyl-1H-imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Teijin Pharma Limited; MARUYAMA, Akinobu; TAKEUCHI, Susumu; TAKAHASHI, Yoshimasa; (30 pag.)EP3144306; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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. Formula: C12H12N2O2

General Procedure 2 (PG 2):3-Methoxy-4-(4-methyl-imidazol-l-yl)-benzaldehyde, phosphonium salt, and lithium hydroxide hydrate were placed in a flask under nitrogen. Solvents were added and the reaction mixture stirred for 16h at room temperature. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine and dried over magnesium sulfate. After solvent evaporation the crude material was purified by chromatography on silica gel.; Example 4 2-{(E)-2-[3-Methoxy-4-(4-methyl-imidazol-l-yl)-phenyl]-vinyl}-lH-benzimidazole Aldehyde (150 mg, 0.69 mmol), phosphonium salt (357 mg, 0.83 mmol), LiOH H2O (87 mg, 2.08 mmol), THF (4.5 mL), and ethanol (1.5 mL) according the GP 2 gave the title compound (178 mg) as a colorless solid after recrystallization from ethyl acetate.1H (600 MHz, dmso-d6): 2.14 (s, 3H), 3.90 (s, 3H), 7.15T7.17 (m, 3H), 7.29-7.34 (m, 3H), 7.39-7.41 (m, 3H), 7.66 (d, J= 16.4 Hz, IH), 7.80 (s, IH).LCMS (ESI): calcd for C20H19N4O [M+H]+ 331.1, found 331.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 870837-18-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/97538; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 28890-99-5, 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. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 104.20 g (10 mmol) 2,8-diiododibenzofuran, 13.0 g (40.0 mmol) caesium carbonate, 1 ,90 g (1.00 mmol) copper(l) 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 24 h at 100 C, filtered and washed with dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is distilled off. The product is crystallized form ether. Yield 4.7 g (81 %)1 H NMR (400 MHz, THF-d8): delta 8.73 (d, J= 1.2 Hz, 2H), 8.14 (d, J= 2.3 Hz, J=8.8 Hz, 2H), 7.96-8.02 (m, 4H), 7.92 (d, J=8.8 Hz, 2H), 7.70-7.73 (m, 2H), 7.62 (d, J= 7.1 Hz, 2H), 7.25- 7.40 (m, 8 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, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; SCHAeFER, Thomas; FIGUEIRA DUARTE, Teresa, Marina; SCHILDKNECHT, Christian; LANGER, Nicolle; HEINEMEYER, Ute; WOLLEB, Heinz; WATANABE, Soichi; LENNARTZ, Christian; WAGENBLAST, Gerhard; WOLLEB, Annemarie; BARDON, Kristina; BENEDITO, Flavio, Luiz; WO2012/130709; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem