Month: April 2021

Synthetic Route of 71759-87-0, These common heterocyclic compound, 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole, 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.

To a solution of 64.3 (0.400g, 1.23mmol, 1.Oeq) 4-iodo- 1-methyl-1H-imidazole (0.306g, 1.47mmol, 1.2eq) in mixture of MeOH (4mL) and dimethoxymethane (lmL). The reaction mixture was degassed by argon for 30 mm. Tetrakis(triphenylphosphine)palladium (0.141 g, 0.1 22mmol, 0.1 eq), Cesium fluoride (0.61 Og, 4.O4mmol, 3.3eq,) was added into reaction mixture and again reaction mixture was degassed by argon for 30 mm. Further reaction mixture was stirred at 150C for 5h. After completion of reaction, water was added to reaction mixture and extracted with ethyl acetate. Organic layers were combined, dried over Na2SO4 and concentrated in vacuo to obtain crude product. This was purified by column chromatography and compound was eluted in 20% ethyl acetate in hexane to obtain64.4 (0.200g, 58.18 %). MS(ES): m/z 281.35 [M+H]t

The synthetic route of 71759-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (869 pag.)WO2018/75937; (2018); 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. 288-32-4, name is 1H-Imidazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H4N2

Reference Example 2 1.3 g of sodium hydride (60%) was added to 10 ml of tetrahydrofuran, and a solution of 2.0 g of imidazole in 10 ml of tetrahydrofuran was added dropwise to the resulting suspension. After 2 hours of stirring at 0 C., the solution was mixed with 1.86 ml of chloroacetonitrile and stirred at room temperature for 3 hours. To the reaction solution was added water and chloroform, and the organic layer was collected and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was subjected to alumina column chromatography eluted with dichloromethane-methanol (200:1) to obtain 1.043 g of 1-cyanomethylimidazole. Mass spectrometry value (m/z): 107 (M+ +1) Nuclear magnetic resonance spectrum (CDCl 3, TMS internal standard) delta: 4.95 (2H, s), 7.06 (1H, d), 7.09 (1H, d), 7.57 (1H, s)

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 288-32-4.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US5565479; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6154-30-9, 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. 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture consisting of 2,5-dibromo-4- nitroimidazole (108.3 g, 400 mmol), ethanol (184 ml), sodium iodide (120 g, 800 mmol) was heated to reflux in an argon stream (65-70C, 26 hours). The reaction mixture was cooled to room temperature and the precipitated inorganic salt was removed by filtration. 78% (234 ml) of the filtrate (300 ml) was concentrated and exsiccated under reduced pressure (25-50C). The residue (brown oil, 172 g) was suspended in chilled water (422 ml), and concentrated hydrochloric acid (10 ml) was added thereto such that the pH of the solution became 1 to 2. The thus obtained solution was further stirred under cooling on ice for 2 hours. Thereafter, the precipitated crystals were collected by filtration and then dried at 50C for 24 hours. Yield: 89.2 g (Yield: 89.9 %), pale yellow crystal IR (KBr): 3218, 1537, 1456, 1386, 1336, 1288, 1250, 1156,1048, 969, 829, 756,731, 665 cm~l MS (70 eV) m/z (relative intensity): 319 (80, M+), 317 (82), 154 (100), 106 (78).

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

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/77913; (2005); 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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 22884-10-2

Trifluoro acetic acid (2 mL) was added dropwise to a solution of 9b (0.505 g, 1.04 mmol) in dichloromethane (8 mL), and the resultant mixture was stirred at room temperature for 3 h. The solution was concentrated to leave 9c (0.52 g, quantitative) as the crystalline trifluoroacetate salt. This was then dissolved into DMF (10 mL) and ^A iisopropylethylamine (3 mL), and the mixture was stirred at room temperature for 10 min followed by treatment with l-ethyl-3_[3- dimethylamino propyl] carbodiimide hydrochloride (EDC HC1; 0.22 g, 1.14 mmol), N- hydroxybenzotriazole (HOBt; 0.175 g, 1.14 mmol) and 2-(lH-imidazol-l-yl)acetic acid (0.197 g, 1.56 mmol; Tokyo Chemical Industry Co. Ltd.). After stirring under N2 for 16 h, DMF was removed in vacuo and the residue was distributed between dichloromethane and 5% aq sodium carbonate. The organic phase was dried and concentrated to an oil that was purified by flash silica gel chromatography eluting with dichloromethane : methanol : NH4OH (95 : 5 : 0.5). Product fractions were pooled and concentrated to give 10 (0.37 g, 72%) as a yellow oil: NMR (CDCI3) delta 7.49 (s, 1 H), 7.36 (m, 5 H), 7.26 (m, 1 H), 7.09 (s, 1 H), 6.95 (s, 1 H), 6.61 (m, 1H), 5.16 (s, 2 H), 4.75 (s, 2 H), 4.07 (t, J= 5.9 Hz, 2 H), 3.62 (m, 2 H), 3.44 (m, 2 H), 2.42 (t, J= 4.9 Hz, 4 H), 2.39 (t, J= 7.2 Hz, 2 H), 1.81 (m, 2 H), 1.62 (m, 2 H); 13C NMR (CDCI3) delta 164.4, 151.3, 150.8, 138.0, 135.6, 131.0, 129.5, 128.7, 128.2, 127.0, 120.1, 105.9, 105.5, 70.9, 69.1, 57.6, 52.6, 47.9, 45.1, 42.3, 26.7, 22.9; MS (ES+) m/z 494.1 (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 22884-10-2.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SHOWALTER, Hollis D.; GARCIA, George A.; XU, Hao; ATWAL, Sumandeep K.; NAWARATHNE, Irosha; KIRCHHOFF, Paul D.; WO2013/86415; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20034-00-8, name is (5-Nitro-1H-benzo[d]imidazol-2-yl)methanol, 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 20034-00-8, Formula: C8H7N3O3

N-Methyl-2-methanol-5-nitrobenzimidazole 53 was prepared according to using the procedure by Harisha et al. [28]. A solution of 5-nitro-(1H-benzimidazole-2-yl)-methanol 30 (0.86 g, 4.50 mmol), and sodium hydroxide (0.18 g, 4.50 mmol) were stirred in dry acetone (20 mL) for 30 min. Then, iodomethane (0.64 g, 4.50 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. The solid was washed with cold water (100 mL) and aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (FAS50) as an yellow crystals Yield 19%.

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:
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

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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H4N2O

An aqueous 30% H2O2 solution (10g) was added dropwise to a stirred solution of imidazole-2-carboxaldehyde (2.88g 0.030mol) in water (10ml). The reaction was allowed to proceed at room temperature for 72h, following which the water was removed in vacuo at room temperature to afford a white crystalline solid. This solid was washed with a stirred mixture of diethylether/water (4:1) to remove the excess peroxide. Note: heating causes decarboxylation. Yield: 97.5%. Mp=156-158C. deltaH (400MHz, D2O): 7.56 (2H, s, Im-H); deltaC (400MHz, D2O): 158.86, 141.02, 120.49ppm. IR nu (KBr): 3392(m), 3124(m), 2861(m), 1618(s), 1502(m), 1462(m), 1421(s), 1388(s), 1322(m), 1108(s), 925(s), 910(s), 819(m), 797(s), 774(m) cm-1. Anal. Calc. for C4H6N2O3 (130.11); C, 36.92; H, 4.65; N, 21.53%. Found: C, 37.18; H, 4.94; N, 21.47%.

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; Gundhla, Isaac Z.; Walmsley, Ryan S.; Ugirinema, Vital; Mnonopi, Nandipha O.; Hosten, Eric; Betz, Richard; Frost, Carminita L.; Tshentu, Zenixole R.; Journal of Inorganic Biochemistry; vol. 145; (2015); p. 11 – 18;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-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 89830-98-8, Product Details of 89830-98-8

General Procedure Synthesis of (1a) To a mixture of 4-cyclopropyl-1H-imidazole (4 g, 37 mmol) and 2-fluoro-5-iodo-4-methyl-benzoic acid (1 eq) in DMSO (200 mL) was added Cu2O (0.05 eq), Cs2CO3 (5 eq) and 8-hydroxyquinioline (0.2 eq) in one portion at 20 C. under N2. The mixture was stirred at 20 C. for 5 min, then heated to 100 C. and stirred for 6 hours. LC-MS showed one main peak with the desired MS. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (SiO2, EtOAc:MeOH:AcOH=1:0:0 to 5:1:0.005) to give 5-(4-cyclopropylimidazol-1-yl)-2-fluoro-4-methyl-benzoic acid (1a). MS mass calculated for [M+1]+ (C14H13FN2O2) requires m/z 261.1, LCMS found m/z 261.1; 1H NMR (400 MHz, DMSO-d6) delta 13.47 (br s, 1H), 8.03-6.96 (m, 4H), 2.20 (s, 3H), 1.94-1.77 (m, 1H), 0.80 (br s, 2H), 0.70 (br s, 2H).

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Terns, Inc.; XU, Yingzi; HALCOMB, Randall; KIRSCHBERG, Thorsten A.; ROMERO, F. Anthony; (117 pag.)US2019/315767; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 39861-21-7, 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 39861-21-7 as follows.

(c) N-[4-(5-Chloro-1H-benzoimidazol-2-yl)phenyl]-2-cyclohexylmethyl-succinamic acid This compound was prepared by the procedure described in Example 1 part (a) from 4-(5-Chloro-1H-benzoimidazol-2-yl) phenylamine and (R)-2-(Cyclohexylmethyl) succinic acid 1-methyl ester to give the crude product (2.0 g, 51%), which was used in the next step without further purification.

According to the analysis of related databases, 39861-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6313117; (2001); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1402838-08-7,Some common heterocyclic compound, 1402838-08-7, name is 2-(1-Trityl-4-imidazolyl)benzaldehyde, molecular formula is C29H22N2O, 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 solution of tert-butyl 5-oxo-2-azaspiro[3.4]octane-2-carboxylate (2 g, 8.89 minol), 2-[ 1 -(triphenylmethyl)- I. H-iniidazol-4-y1]benzaldehyde (5.53 g, 13.34 mmol) and Ca(OH)2 (1.64g. 22.13 mniol) in EtOH (250 mL) was stirred for 6 hat 80C. The solids were filtered out. The solids were filtered out. The solvent was concentrated under vacuum. The residue was purified by silica gel column eluting with EtOAc /PE (1:2). This resulted in 5.24 g (95%) of tert-butyl (6E)-5-oxo-6-([2-[ 1 -(triphenyl.methyl)-1 H-imidazoi-4-yljphenyljmethylidene)-2-azaspiro[3.4]octane-2-carboxylate as a light yellow solid. LCMS (ESI)mJz = 622.8 [.M+Hr.

The synthetic route of 1402838-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; PEI, Zhonghua; PASTOR, Richard; GAZZARD, Lewis; PARR, Brendan; LIU, Wendy; MENDONCA, Rohan; WU, Guosheng; YUEN, Po-Wai; (183 pag.)WO2019/5559; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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.

General procedure: A mixture of the corresponding 2-amino-4-arylimidazole 1(1.0 mmol), aromatic aldehyde 2 (2.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products 16were filtered off and crystallized from iPrOH. 16a: yellowpowder, 30%, mp 239-240 C; 1H NMR (200 MHz, DMSO-d6)delta 9.32 (s, 1H, CHazomethine), 8.12 (d, J = 6.7 Hz, 2, Ar),7.67-7.45 (m, 5, Ar), 7.27-7.04 (m, 10, C5NH2, Ar), 5.15(s, J = 6.7 Hz, 1H, C7H), 4.05-3.84 (m, 2, 23), 1.01(s, J = 7.0, 3H, 2CH3); 13C NMR (125 MHz, DMSO-d6) delta178.7 (CO), 134.5, 133.3, 130.2, 129.6, 128.7, 128.6, 128.3, 127.8, 127.2, 127.0, 126.4, 125.8, 125.5, 116.7, 93.4, 58.9, 43.4,14.7; MS (m/z) (%): 448 ([M+?], 100; anal. calcd. forC28H24N4O2 (448.19) C, 74.98; H, 5.39; N, 12.49; found: ,75.12; H, 4.89; N, 11.37.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem