Tag: M.W=100-200

Synthetic Route of 7189-69-7,Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, 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.

0.18 g (1.20 mmol) of 2-hydroxyl-N-methylbenzenecarboximidamide is stirred with 0.48 g (2.42 mmol) of 1,1′-sulphonyldiimidazole at 120 C. for 18 hours. Cooling is followed by stirring the mixture with water and then decanting off from the water. The remaining residue is chromatographed on silica gel (450 g, 40-63 mum) with dichloromethane/methanol=99/1. 87 mg of product are isolated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1′-Sulfonyldiimidazole, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; US2010/267703; (2010); 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. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Safety of 7-Nitro-1H-benzo[d]imidazole

(Step 1) tert-Butyl 4-nitro-1H-benzimidazole-1-carboxylate To a suspension of 4-nitro-1H-benzimidazole (2.65 g) in tetrahydrofuran (80.0 mL), triethylamine (3.38 mL) and di-tert-butyl dicarbonate (4.25 g) were added, and the mixture was stirred at room temperature for 1 hour. 4-Dimethylaminopyridine (0.0397 g) was then added to the mixture, and the resultant mixture was stirred at room temperature overnight. After the reaction solution was concentrated under reduced pressure, the residue obtained was purified by silica gel column chromatography (chloroform/ethyl acetate). After concentration under reduced pressure, diethyl ether was added to the solid obtained to obtain a suspension, and the suspension was filtered off and dried to obtain the title compound (3.94 g) as a solid. 1H-NMR (CDCl3) delta: 1.73 (9H, s), 7.53 (1H, t, J = 8.2 Hz), 8.20-8.22 (1H, m), 8.39-8.41 (1H, m), 8.62 (1H, s). MS (m/z) :164 (M-CO2tBu+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 10597-52-1.

Reference:
Patent; Daiichi Sankyo Co., Ltd.; NAITO, Hiroyuki; KAGOSHIMA, Yoshiko; FUNAMI, Hideaki; NAKAMURA, Akifumi; ASANO, Masayoshi; HARUTA, Makoto; SUZUKI, Takashi; WATANABE, Jun; KANADA, Ryutaro; HIGUCHI, Saito; ITO, Kentaro; EGAMI, Akiko; KOBAYASHI, Katsuhiro; EP3643703; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 41716-18-1, 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 41716-18-1 as follows.

To a solution of tert-butyl (1-(4-(5-hydrazono-3-phenyl-5,6,7,8-tetrahydro-1,6- naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (22mg, 0.04 mmol) in dry DMF (1 ml_) was added EDCI (11 mg, 0.06 mmol), HOBt.H20(8 mg, 0.06 mmol) and 1-methyl-1H- imidazole-4-carboxylic acid (8 mg, 0.06 mmol) under nitrogen. The reaction mixture was heated at 60 °C overnight. After cooled down to room temperature, the mixture was partitioned between saturated NaHC03 solution and ethyl acetate. The layers were separated and the organic phase washed with water and brine, dried over Na2S04, filtered and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95percent 0.1percentFA/ACN in0.1percentFA/H2O) to give the title compound (1 mg, 5percent). NMR (500 MHz, CDCI3): 8.49 (1 H, s), 7.74 (1 H, s), 7.54 (1H, s), 7.38 (2H, d), 7.31 (2H, d), 7.28-7.23 (5H, m), 5.01 (1 H, br s), 4.94 (2H, t), 3.81 (3H, s), 3.49 (2H, t), 2.60-2.30 (4H, m), 2.10-2.01 (1 H, m), 1.85- 1.76 (1 H, m), 1.45-1.20 (9H, br).

According to the analysis of related databases, 41716-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMAC DISCOVERY LIMITED; ZHANG, Lixin; TREVITT, Graham, Peter; MIEL, Hughes; BURKAMP, Frank; HARRISON, Timothy; WILKINSON, Andrew, John; FABRITIUS, Charles-Henry; WO2011/77098; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 405173-97-9, 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. 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-(2-Aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4-carboxamide dihydrochloride (103) (2.0 g, 3.96 mmol) was added to a solution of 2-(2-chloroethyl)-1 H-1 ,3-benzodiazole hydrochbride (1.12 g, 5.15 mmol) and DIPEA (10.6 ml, 59.45 mmol) in DMF (60 ml). The reaction mixture was allowed to stir at 3GC for 6 d (reaction was monitored by LCMS). The mixture was concentrated in vacuo and the residue was neutralised using sat. NaHC03 (aq). The aqueous layer was extracted using 4: 1 CHCb / 1 PA (4 x 100 ml) and the combined organic layers were dried (MgS04), filtered and evaporated in vacuo. The crude residue was purified by flash column chromatography (kp-NH, eluting with a gradient of 60-100% EtOAc / heptane followed by 0-20% MeOH / EtOAc) follow by neutral reverse-phase column chromatography (gradient elution 0-60% MeCN / water) to give the title compound (0.173 g, 10%) as a yellow oil. 1 H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 (d, J = 4.6 Hz, 1 H), 8.02 (s, 1 H), 7.57 (t, J = 9.1 Hz, 1 H), 7.45 – 7.40 (m, 2H), 7.36 (dd, J = 8.6, 4.3 Hz, 1 H), 7.17 (dd, J = 6.0, 3.2 Hz, 2H), 4.68 (s, 2H), 3.26 (d, J = 6.8 Hz, 2H), 3.15 – 3.07 (m, 6H) HPLCMS (Method D): [m/z]: 425.1 [M+H]+In a similar fashion using general procedure 7, 1-(2-aminoethyl)-N-[(3-chloropyridin-2-yl)methyl]-1H- pyrazole-4-carboxamide dihydrochloride (261) (0.45 g, 1.28 mmol), 2-(2-chloroethyl)-1H-benzimidazole (0.28 g, 1.53 mmol) and DIPEA (3.3 ml, 19.14 mmol) in DMF (7 ml) at room temperature for 66 h, then heated to 40C for 90 h, gave the title compound (112 mg, 21%) as a colourless film after purification by flash column chromatography (kp-NH, eluting with a gradient of 0-10% MeOH / DCM) followed by basic prep-HPLC. 1H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.10 (s, 1H), 8.52-8.44 (m, 2H), 8.22 (s, 1H), 7.92 (dd, J = 8.1, 1.4 Hz, 1H), 7.90 (s, 1H), 7.55-7.38 (br m, 2H), 7.37 (dd, J = 8.1, 4.7 Hz, 1H), 7.13- 7.07 (m, 2H), 4.63 (d, J = 5.7 Hz, 2H), 4.20 (t, J = 6.2 Hz, 2H), 2.99- 2.93 (m, 4H), 2.93 – 2.89 (m, 2H) HPLCMS (Method C): [m/z]: 424.1 [M+H]

The chemical industry reduces the impact on the environment during synthesis 2-(2-Chloroethyl)-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 68282-47-3, 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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 4-Formyl-2-phenyl-imidazole-1-carboxylic acid 4-nitro-benzyl ester 4-Formyl-2-phenylimidazole (624 mg) and sodium hydrogen carbonate (791 mg) were dissolved in dioxane (3.6 mL), THF (3.6 mL) and water (7.2 mL). The 48.7% solution of p-nitrobenzyl chloroformate (PNZCl) in dioxane (2.08 mL) was added to the mixture at room temperature and stirred for 2.5 h. The mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from ethyl acetate and n-hexane to give the title compound (956 mg, 75%). 1H NMR (delta, CDCl3) 5.41 (s, 2H), 7.32 (d, 2H, J=8.6 Hz), 7.40-7.51 (m, 3H), 7.56-7.58 (m, 2H), 8.17-8.20 (m, 2H), 8.22 (s, 1H), 9.97 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Phenyl-1H-imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2004/132708; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9, 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. 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: All complexes were prepared by a similar procedure. A mixture of Ln(NO3)3 [Ln=Eu3+ (1), Tb3+ (2), Er3+ (3), Nd3+ (4)] (0.10mmol), H3IDC (0.12mmol), 4,4-bipy (0.10mmol), DMF (2mL), and H2O (15mL) was adjusted to pH=3 with acetic acid and then placed in a sealed Teflon-lined stainless steel vessel (25mL), which was heated at 160C for 3d. Then the reaction system was cooled to room temperature over 2d at a rate of 5C/h to give block crystals of 1-4, respectively.

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, 1H-Imidazole-4,5-dicarboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jin, Jun-Cheng; Tong, Wen-Quan; Fu, Ai-Yun; Xie, Cheng-Gen; Chang, Wen-Gui; Wu, Ju; Xu, Guang-Nian; Zhang, Ya-Nan; Li, Jun; Li, Yong; Yang, Peng-Qi; Journal of Solid State Chemistry; vol. 225; (2015); p. 216 – 221;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 6775-40-2, 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. 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

The chemical industry reduces the impact on the environment during synthesis 5-Phenyl-1H-imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1848-84-6,Some common heterocyclic compound, 1848-84-6, name is 2-Ethyl-1H-benzo[d]imidazole, molecular formula is C9H10N2, 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 solution of 10.0 mmol of compound 1a-1d in 14 mL of concentrated sulfuric acid was heated to 100-105C, 14 mL (0.26 mol) of 30% aqueous hydrogen peroxide was added dropwise with stirring,and the mixture was stirred for 1 h at 130C. After cooling, the mixture was poured into water and adjusted to pH 4, and the precipitate was filtered off.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethyl-1H-benzo[d]imidazole, its application will become more common.

Reference:
Article; Brusina; Nikolaev; Ramsh; Piotrovskii; Russian Journal of Organic Chemistry; vol. 52; 10; (2016); p. 1528 – 1530; Zh. Org. Khim.; vol. 52; 10; (2016); p. 1533 – 1535,3;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39021-62-0, The chemical industry reduces the impact on the environment during synthesis 39021-62-0, name is 1-Methyl-1H-imidazole-5-carbaldehyde, I believe this compound will play a more active role in future production and life.

EXAMPLE 6A 1-(1-methyl-1H-imidazol-5-yl)-3-phenylprop-2-yn-1-ol A suspension of 1-methyl-1H-imidazole-5-carbaldehyde (prepared according to the procedure described in J. Org. Chem. 1993, 58, 1159-1166, 170 mg, 1.55 mmol) in dioxane (10 mL) was treated with 1M phenylethynylmagnesium bromide in THF (7.73 mL, 7.73 mmol), heated to 80 C. for 1 hour, cooled to room temperature, treated with brine, and extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2% methanol/ethyl acetate with 0.2% NH4OH to provide the desired product (210 mg, 64%). MS (DCI/NH3) m/e 213 (M+H)+; 1H NMR (300 MHz, CDCl3) delta7.52 (s, 1H), 7.47 (m, 2H), 7.34 (m, 3H), 7.15 (s, 1H), 5.74 (s, 1H), 3.83 (s, 3H).

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, 1-Methyl-1H-imidazole-5-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gwaltney II, Stephen L.; Nelson, Lissa T.J.; O’Connor, Stephen J.; Sham, Hing L.; Sullivan, Gerard M.; Wang, Weibo; US2003/216441; (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. 934-22-5, name is 6-Aminobenzimidazole, A new synthetic method of this compound is introduced below., name: 6-Aminobenzimidazole

General procedure: A dry 50 mL flask was charged with 2-halogenated aromatic aldehyde 1 (1.0 mmol), 1H-benzo[d]imidazol-5-amine (0.133 g,1.0 mmol), cyclohexane-1,3-diones (1.0 mmol), CuI (10 mg), L-proline(6 mg), Cs2CO3 (650 mg) and dioxane (10 mL). The reaction mixture was stirred at reflux for 10-18 h. After completion of the reaction, as indicated by TLC, the solid was filtered off by a fast and hot filtration, and the products of 4 were obtained as pale yellow powder or crystals, when the mixture was allowed to cool down to room temperature.

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; Li, Chao; Zhang, Wen-Ting; Wang, Xiang-Shan; Tetrahedron; vol. 70; 46; (2014); p. 8919 – 8924;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem