Author: Jessica.F

5465-29-2, name is 2-Propylbenzimidazole, 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. Product Details of 5465-29-2

[step 2] (Z)-2-(2-Hydroxymethyl-5,11-dihydrobenzooxepino[3,4-b]pyridine)propiononitrile (0.111 g, 0.396 mmol) obtained in step 1 was dissolved in THF (2 mL), 2,6-lutidine (0.276 mL, 2.37 mmol), lithium bromide (0.206 g, 2.37 mmol) and methanesulfonic anhydride (0.172 g, 0.989 mmol) were added and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. 2-Propylbenzimidazole (0.053 g, 0.333 mmol) was dissolved in DMF (2 mL), potassium carbonate (0.218 g, 1.58 mmol) was added and the mixture was stirred for 15 min. To this mixture was added the residue obtained above, and the mixture was stirred at 60C for 2 hr. Water was added to the mixture and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated Under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to give (Z)-2-[2-(2-propylbenzimidazol-1-yl)methyl-5,11-dihydrobenzooxepino[3,4-b]pyridine]propiononitrile (0.094 g, 56%).

The synthetic route of 5465-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2327690; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26832-08-6, These common heterocyclic compound, 26832-08-6, name is 1H-Imidazole-4-carboxamide, 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.

D2O, H2O2 (30%), NaCl, NH4VO3 and ima were commercial products (Shanghai DingmiaoChemistry Co., Ltd) and used without purification. The ionic medium 0.15 mol L-1 NaCl/D2Osolution at 25 C was chosen to represent physiological conditions, in all solution NMR experiments.To form the ternary system of NH4VO3/H2O2/ima, NH4VO3 and H2O2 were first mixedin a 1:5 molar ratio in D2O to produce the species [VO(O2)2(D2O)]-/[VO(O2)2(HOD)]- followedby the addition of ima. Unless otherwise stated, the total concentration of vanadate specieswas 0.1 mol L-1. The NMR samples were allowed to stand at least 4 h to let the coordinationreactions reach equilibrium.The bisperoxovanadium crystals of 1 were prepared by adding 10 mL of H2O2 (30%, w/v,solution) and 1.17 g NH4VO3 to 50 mL distilled water. After NH4VO3 was dissolved, 1.11 g imawas added to the mixture. The mixture was stirred in an ice bath at 273 K for 0.5 h. The reactionmixture was then filtered and the solution was kept at 278-283 K for one week tocrystallize. The crystals were recovered by filtration and washed with 3 mL of cold water and5 mL of cold ethanol and then dried on a filter paper. Yield: ca. 50-70% (based on NH4VO3).

The synthetic route of 26832-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Shaowei; Xia, Wen; Yang, Yueyue; Yu, Xianyong; Li, Xiaofang; Journal of Coordination Chemistry; vol. 70; 17; (2017); p. 2958 – 2968;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, 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 2620-76-0, HPLC of Formula: C19H13BrN2

The solution of n-BuLi in 2.5Mn-hexane (2.64 mL,6.6 mmol)was added dropwise to a solution of 2-(4-bromophenyl)-1-phenyl-1H-benzo[d] imidazole (2.09 g, 6 mmol) in dry THF(30 mL) at 78 C. At temperature of 78 C, the resulting reactionmixture was stirred continuously. Thereafter, we slowly added trimethylchlorosilane(0.76 mL, 6 mmol) to the mixture. Then, thereaction temperature was allowed to warm at room temperatureand stirred overnight. The reaction was quenched by adding water, and the crude product was extracted twice using 100 mL ofdichloromethane. Finally, the crude productwaswashed with brine.The combined organic layer was dried over MgSO4 and subjected tofiltration. The filtrates were dried under reduced pressure, and theresidue was subjected to column chromatography using ethyl acetate/n-hexane (v:v 1:10) as an eluent. Compound 1 was obtainedas a white solid with yield of 78%. We could not perform train sublimationof compound 1 due to its poor thermal stability.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yi, Seungjun; Kim, Jin-Hyoung; Bae, Woo-Ri; Lee, Jiwon; Han, Won-Sik; Son, Ho-Jin; Kang, Sang Ook; Organic electronics; vol. 27; (2015); p. 126 – 132;,
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. 716-79-0, name is 2-Phenyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C13H10N2

The synthesis of 1-methyl-2-phenyl-1H-benzoimidazole (Mpb) is accomplished by referring to methods disclosed in Popov, 1. I., Chem. Heterocycl. Compd. (EN), 1996, 32, 6, p.672-681. The synthetic method is outlined in Scheme 1. To 20 mL acetone was added 2-phenyl-1H-benzoimidazole (1.94 g, 10 mmol), followed by the injection of iodomethane (1.42 mL, 12 mmol). The mixture was stirred at room temperature for 6 h, sodium hydroxide solution was then added, and the mixture reacted for an additional 5 min. The reaction mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using n-hexanes/EA (v/v=80/20) as eluent. After the product was completely isolated, 1.03 mg (0.49 mmol) of the title compound was obtained (49percent yield). 1H NMR (CDCl3, delta): 3.87 (s, 3 H), 7.32-7.41 (m, 3 H), 7.51-7.56 (m, 3 H), 7.83-7.86 (m, 3 H).

According to the analysis of related databases, 716-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cheng, Chien-Hong; Chen, Ruey-Min; Guo, Hong-Ru; Chung, Jun-Wen; US2005/116626; (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. 3304-70-9, name is Dimethyl 4,5-imidazoledicarboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 3304-70-9

(1) Dimethyl 1H-imidazole-4,5-dicarboxylate (9.6 g, 52 mmol) was dissolved in acetonitrile (200 mE), and N-bromosuccinimide (13.92 g, 78 mmol) was added thereto, and then the mixture was stirred at 50 C. for 4 hours. After the reaction, water was added and the mixture was extracted twice with ethyl acetate. After being washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride, the organic layer was dried over anhydrous sodium sulfate. The organic layer was concentrated to obtain dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate (8.3 g). This material was used as is in the next reaction without further purification:10217] ?H-NMR (CDC13) oe: 10.56 (1H, s), 3.96 (6H, s);10218] ESI-MS mlz=263 (M+H).

The synthetic route of 3304-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 219814-29-6,Some common heterocyclic compound, 219814-29-6, name is 2,5-Dibromo-4-methylimidazole, molecular formula is C4H4Br2N2, 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.

Step A : (5-Bromo-6-methyl-3 H- 1 ‘ -azaspiro [imidazo [2, 1 -b] oxazole-2,3 ‘ – bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate and (6-bromo-5-methyl-3H-l ‘- azaspiro[imidazo[2, l-b]oxazole-2,3 ‘-bicyclo[2.2.2]octan]- -yl-8-ium)trihydroborate To 2,4-dibromo-5-methyl-lH-imidazole (0.8 g, 3.3 mmol) in THF (25 niL) was added N-butyllithium (1.3 niL, 3.3 mmol) dropwise at -78C. After 45 minutes, a solution of racemic r-azaspiro[oxirane-2,3′-bicyclo[2.2.2]octan]-l’-yl-4- ium)trihydroborate (0.56 g, 3.7 mmol) from the reference example, in THF (20 mL) was added dropwise at -78C. The cooling bath was removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield the regioisomeric products. These regioisomers were separated by reverse phase chromatography using a Sunfire column with gradients of acetonitrile-water containing 0.1% of trifluoroacetic acid (TFA), and at 40 mL/min flow rate. The pure fractions for peak 1 and peak 2 were then neutralized with 1 N NaOH (pH ~8-9) and the products were extracted with ethyl acetate. The organic layers were dried with MgS04, filtered and the solvent was removed to yield racemic (5-bromo-6-methyl-3H-l’-azaspiro[imidazo[2,l-b]oxazole-2,3′- bicyclo[2.2.2]octan]-l’-yl-8-ium)trihydroborate (0.32 g, 1.0 mmol, 30.8 % yield) XH NMR (500MHz, DMSO-d6) delta 4.23 (d, J=9.8 Hz, IH), 4.12 (d, J=9.9 Hz, IH), 3.36 (dd, J=15.2, 2.5 Hz, IH), 3.19 (dd, J=15.3, 2.1 Hz, IH), 3.04 – 2.95 (m, IH), 2.91 – 2.73 (m, 3H), 2.35 (br. s., IH), 2.03 – 1.88 (m, 4H), 1.84 – 1.67 (m, 3H), 1.64 – 1.11 (m, 3H). MS (LC/MS) R.T. = 2.09; [M+2]+ = 300.04 and racemic (6-bromo-5-methyl-3H-l’- azaspiro[imidazo[2,l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r-yl-8-ium)trihydroborate (0.33 g, 1.1 mmol, 31.7 % yield) as powders. NMR (500MHz, DMSO-de) delta 4.32 (d, J=10.1 Hz, IH), 4.12 (d, J=10.2 Hz, IH), 3.36 (d, J=2.4 Hz, IH), 3.18 (dd, J=15.2, 2.2 Hz, IH), 2.99 (d, J=2.9 Hz, IH), 2.93 – 2.78 (m, 3H), 2.31 (d, J=2.0 Hz, IH), 2.06 – 1.94 (m, 4H), 1.84 – 1.69 (m, 3H), 1.62 – 1.22 (m, 3H). MS (LC/MS) R.T. = 2.64; [M+2]+ = 300.04.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-methylimidazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); 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. 147403-65-4, name is Methyl 2-ethoxy-1-((2′-(N-hydroxycarbamimidoyl)-[1,1′-biphenyl]-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate, A new synthetic method of this compound is introduced below., Formula: C25H24N4O4

Methyl 2-ethoxy- l -((2′-(5-oxo-4,5-dihydro- l ,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- l H- benzo[< ]imidazole-7-carboxyiate of formula la - reproduction of the procedure (J. Med. Chem. 1996, 39(26), 5228-5235)2-ethylhexyl chloroformate (0.25 g, 2.6 mmol) was added to a stirred mixture of methyl 2- ethoxy- l -((2'-((hydroxyamino)iminomethyl)biphenyl-4-yl)methyl)- l H-benzo[i/]imidazole-7- carboxylate (of formula Va; 1.16 g, 2.6 mmol), dry DMF (5 ml) and pyridine (0.22 g) under cooling in a water-ice mixture and the mixture was stirred at the temperature of 0C for 30 minutes. After dilution with water (20 ml) the mixture was extracted with ethyl acetate (4 x 10 ml), the extract was washed with water (4 x 5 ml) and dried with MgS04. The obtained evaporation residue ( 1.7 g) contained 92.2 % of the intermediate (of formula VI; R' = 2- ethylhexyl) according to HPLC. 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:
Patent; ZENTIVA, K.S.; RADL, Stanislav; STACH, Jan; WO2012/139535; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39513-26-3, A common heterocyclic compound, 39513-26-3, name is 5-Bromo-1,3-dihydrobenzoimidazol-2-one, molecular formula is C7H5BrN2O, 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.

Example 1095 Step 1 A solution of Compound 1095A in DMF (2 ml) was treated sequentially with sodium hydride (28 mg, 60% dispersion in oil, 0.70 mmol) and iodomethane (0.04 ml, 80 mg, 0.56 mmol). The reaction mixture was stirred overnight at rt. The reaction was quenched with water, diluted with EtOAc, and washed sequentially with water and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give crude Compound 1095B (37 mg, 68%), which was used without further purification.

The synthetic route of 39513-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/84451; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, 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. Safety of 5-Bromo-1H-benzo[d]imidazole

To a solution of 3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]benzaldehyde and 3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]benzaldehyde (0.22 g, 0.47 mmol) in dichloromethane (5 mL) was added 1 drop of acetic acid, followed by 4,4-dimethylcyclohexylamine hydrochloride (78 mg, 0.47 mmol) and triethylamine (66 muL, 0.47 mmol). NOTE: If a free amine was used, triethylamine was not added. After stirring 60 min at room temperature, sodium triacetoxyborohydride (0.40 g, 1.9 mmol) was added and the reaction was stirred an additional 3 h. The reaction mixture was diluted with H2O and CH2Cl2. The layers were separated and the aqueous layer was extracted 2× CH2Cl2. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo. Chromatography provided the reductive amination product as a mixture of trityl regioisomers, (4,4-dimethylcyclohexyl)({3-[1-(triphenylmethyl)-1H-benzimidazol-6-yl]phenyl}methyl)amine and (4,4-dimethylcyclohexyl)({3-[1-(triphenylmethyl)-1H-benzimidazol-5-yl]phenyl}methyl)amine. (M+1) 576.4 ES, 2.40 min and 2.51 min (LC/MS Method A).

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 496-46-8, 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 496-46-8 as follows.

Into a suitable reaction vessel equipped with a stirrer, thermometer and reflux condenser, there was introduced 688 parts (10 mol) of aqueous formaldehyde (44%), and the pH was adjusted to 8.7 with 22 parts of 0.5 N NaOH solution. To this solution, there was added 284 parts (2 mol) of acetylene carbamide at 40 C. During the resulting reaction, the temperature was allowed to rise up to 55 C. At this stage, most of the acetylene carbamide entered into solution. After about 15 minutes, the pH was adjusted to 8.0 with five parts of 0.5 N NaOH. A clear, pale yellow colored solution was obtained. The clear solution was distilled at 50 C, under reduced pressure, to remove water until the reaction vessel content was about 640 parts. The resulting syrup in the vessel was poured into 800 parts of methanol. The resulting white crystalline precipitate was filtered and dried. The total yield of the tetramethylol acetylene carbamide was 483 parts (92%) and had a melting point of 132 – 136 C.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED; BRISTOW, James Timothy; WO2014/166347; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem