Month: November 2020

288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

200.0 ml (1.84 mol) of N,N-dimethylsulfamoyl chloride,147.0 g (2.16 mol) of imidazole and 280 ml of triethylamine were added to 2.5 L of anhydrous diethyl ether with stirring.Stir at room temperature for 16 h. After the reaction is completed, the reaction solution is filtered.The filter cake was washed with 1.5 L of diethyl ether.The filtrate was combined and the filtrate was dried over anhydrous Na Residues, distillation residues to obtain products:305.1g.(0.4 mmHg), placed to form a colorless crystal.Yield: 94.75%

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chenxin Pharmaceutical Co., Ltd.; Wang Qianying; Bie Fenxia; Gong Ruo; Li Zhongjing; Jiang Ruiling; (7 pag.)CN109608400; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-02-9, Adding a certain compound to certain chemical reactions, such as: 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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 152628-02-9.

Example 3 Preparation of f4′ – [2-n-propyl-4-methyl-6-(1-methyl benzimidazol-2-vl) benzimidazol -1-vl methvll biphenvl-2-carboxvlic acidl 50 gm of [1 H – Benzimidazole-2-n – propyl-4-methyl-6-(1′-methyl benzimidazole-2′- yl) ] was added to 200 ml dimethyl sulfoxide and 50 gm of sodium hydroxide. To this was added 60 gm of methyl-4- (bromomethyl) biphenyl-2-carboxylate at ambient temperature. The contents were stirred for 2 hours at 25-30 C and then heated to 40-50 and maintained for 2 hours. About 500 ml water was added to the reaction mixture and acidified with acetic acid to pH 4.2, extract4ed twice with 250 ml of dichloromethane and the combined extracts were concentrated and isolated by filtration after addition of 300 ml acetone, dried under reduced pressure at 50-60 C to give 75.0 gm (80%) of the title compound.

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIPLA LIMITED; TURNER, Craig, Robert; WO2005/108375; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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 41716-18-1. 41716-18-1

1-methyl -1H- imidazole-4-carboxylic Acid (1eq) was dissolved in dimethylformamide (DMF) and, morpholine (1.01 eq) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide imide was added dropwise (EDC, 1.1 eq), 1- hydroxybenzotriazole (HOBT, 1.1 eq) and triethylamine (TEA, 3 eq) in sequence. After stirring overnight at room temperature, then terminate the reaction with a small amount of water, extracted with EtOAc and water and a small amount of water in the organic layer was removed by using anhydrous MgSO4, and evaporated under reduced pressure to remove the solvent and dried in vacuo. Then, separated by column to give the title compound in 45percent yield.

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 1-Methyl-1H-imidazole-4-carboxylic acid.

Reference:
Patent; THE INDUSTRY & ACADEMIC COOPERATION IN CHUNGNAM NATIONAL UNIVERSITY (IAC); KIM, EUN HEE; YOO, SUNG EUN; KANG, NAM SOOK; KOO, TAE SUNG; PARK, MIN YOUNG; KIM, YOUNG HOON; BAE, HYUN JU; KIM, JIN WOO; IN, TAE KYU; JOO, CHOUN KI; (25 pag.)KR101555033; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

152628-03-0, 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. 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 1 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic Acid Methyl Ester 7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30.0 g, 137 mmol) was dissolved in MeOH (550 mL) and added to a round bottom flask, followed by the addition of 20 mL of a hydrogen chloride solution (30:70, conc. HCl:water). The mixture was refluxed for 12 hours then concentrated under reduced pressure to afford the title compound as a yellow solid (31.8 g, 137 mmol). MS m/z: [M+H+] calcd for C13H16N2O2, 233.12; found 233.2.

The synthetic route of 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theravance, Inc.; US2008/318951; (2008); 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. 2034-23-3, name is 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., 2034-23-3

Preparation of 6-chloro-l -( 3-chloropropyl)-lH-benzo[Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To the solution of PdCl2(PPh3)2 (0.050 g, 0.07 mmol) dissolvedin 10 mL of CH3CN, bzimSH (0.021 g, 0.14 mmol) was added followedby Et3N base (0.5 mL). The solution became turbid and yellowishorange in color. Then the refluxing was done for 6 h. Thecolor of the reaction mixture became orange and was filtered.The filtrate was evaporated using rotary evaporator until a solidwas obtained. It was treated with acetone which dissolved thecomplex leaving behind Et3NH+Cl, white solid. The acetone solutionwas filtered to remove Et3NH+Cl. To it was added 4 mLdichloromethane-methanol (1:1, v/v) mixture and left to evaporateat room temperature. The orange colored crystals of compound2 were formed in a period of 10-15 days (67%, m.p 218-220 C). Anal. Calc. for C75H61ClN6P3Pd2S32H2O (1519.67): C,59.22; H, 4.01; N, 5.53. Found: C, 59.80; H, 4.36; N, 5.52%. IRbands(KBr, cm1): nu(O-H), 3393m (b); m(C-H), 3051m, 2963w; nu(C-C) + nu(C-N) + delta(C-H), 1618s, 1479m, 1433s, 1391s, 1263m,1226w;, 1182 w; nu(P-CPh), 1096s; nu(C-S) 1022s; 802m, 741s,691s, nu(Pd-N), 523s; 422w. ESI Mass could not be recorded dueto poor solubility.

The synthetic route of 2-Mercaptobenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lobana, Tarlok S.; Sandhu, Amanpreet K.; Mahajan, Rakesh K.; Hundal, Geeta; Gupta, Sushil K.; Butcher, Ray J.; Castineiras, Alfonso; Polyhedron; vol. 127; (2017); p. 25 – 35;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, Name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 496-46-8, 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.

Synthesis of cucurbit[n]urils in methanesulphonic acid usingDipropoxymethane (Propylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Propylal (45 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a beige powder which was analysed by1H NMR. Approximate Yields by1H NMR (% of recovered product) cucurbit[5]urii 0%, cucurbit[8]uril 58%, cucurbit[7]uril 42%, cucurbit[8]uril 0%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[11]urii 0%. Residual formaldehyde by HPLC method was 5 ppm.

Statistics shows that Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is playing an increasingly important role. we look forward to future research findings about 496-46-8.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., 22884-10-2

48.87 g (0.4 mol) of 3,4-diaminotoluene and 63.05 g (0.5 mol) of 1-imidazole-1-acetic acid were weighed into a 1000 mL three-necked flask and 375 mL of 4 mol / L hydrochloric acid was added The mixture was stirred for 20 h at room temperature. The solution was reddish-brown and then refluxed at 100 C for 15 h. The solution gradually deepened and finally dark brown. After cooling, the reaction solution was poured into 1000 mL of distilled water and adjusted to pH 7-8 with ammonia. A large amount of precipitate was collected, suction filtered and then recrystallized from hot water to obtain 33.02 g of yellow crystals (yield: 38.89%).

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; Henan Polytechnic Institute; Huang, Qiuying; Lin, Xichang; Yang, Yi; Liu, Wei; Liu, Chunli; Su, Mingyang; Chen, Xiaodong; Du, Xikun; Shen, Gang; Fang, Lei; Meng, Xiangru; (8 pag.)CN104610310; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10111-08-7, 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. 10111-08-7 name is Imidazole-2-carboxaldehyde, 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.

Reference Example 27 Synthesis of ethyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0418) (0419) Potassium carbonate (1.44 g, 10.4 mmol), ethyl chloroacetate (0.585 mL, 5.46 mmol), and potassium iodide (0.864 g, 5.20 mmol) were added to a solution of 1H-imidazole-2-carbaldehyde (0.500 g, 5.20 mmol) in N,N-dimethylformamide (10.0 mL) at room temperature, the temperature of the reaction liquid was raised to 90 C., and the reaction liquid was stirred for 4 hours. Distilled water was added to the reaction liquid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, chloroform/methanol) to obtain ethyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.269 g, 1.48 mmol, 28%) as a yellow oil. (0420) 1H-NMR (400 MHz, CDCl3) delta: 1.29 (3H, t, J=7.2 Hz), 4.25 (2H, q, J=7.2 Hz), 5.14 (2H, s), 7.15 (1H, brs), 7.33 (1H, s), 9.79-9.91 (1H, m). (0421) ESI-MS: m/z=183 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Imidazole-2-carboxaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Toray Industries, Inc.; MORITA, Yasuhiro; IZUMIMOTO, Naoki; ISEKI, Katsuhiko; IWANO, Shunsuke; UDAGAWA, Shuji; MIYOSHI, Tomoya; OSADA, Yuji; KOREEDA, Tetsuro; MURAKAMI, Masanori; SHIRAKI, Motohiro; TAKAHASHI, Kei; OSHIDA, Keiyu; (91 pag.)US2016/194302; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

7720-39-0, Adding some certain compound to certain chemical reactions, such as: 7720-39-0, name is 1H-Imidazol-2-amine, 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 7720-39-0.

Example 24 (S)-3-Cyclohexyl-N-(1H-imidazol-2-yl)-2-(1-oxo-1,3-dihydro-isoindol-2-yl)propionamide BOP coupling of (S)-3-Cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (prepared in Example 1, Step A; 287 mg; 1.00 mmol) and 2-aminoimidazole (241 mg; 1.79 mmol) in a manner similar to that used for the preparation of (S)-3-cyclohexyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-N-thiazol-2-yl-propionamide (outlined in Example 1, Step B) provided after flash chromatography (Biotage 40M; eluent: 4% methanol/methylene chloride) 320 mg of (S)-3-Cyclohexyl-N-(1H-imidazol-2-yl)-2-(1-oxo-1,3-dihydro-isoindol-2-yl) propionamide which was then recrystallized from ethyl acetate/hexanes to give 209 mg of pure material: EI-HRMS m/e calcd for C20H24N4O2 (M+) 352.1899, found 352.1895.

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 7720-39-0.

Reference:
Patent; Guertin, Kevin Richard; US2002/82260; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem