Author: Jessica.F

152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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. 152628-02-9

In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2′- cyanobiphenyl was added. The reaction mass was warmed to 80 C and maintained for 4 hours at 80 to 85 C. The completion of the reaction was monitored by TLC using mobile phase chloroform : methanol (9:1). After completion of the reaction, the mass was cooled to 20 C, maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4′-(2″-n-propyl-4″-methyl- 6″-(r”-methylbenzimidazol-2″‘-yl)benzimidazol-l”- ylmethyl) biphenyl, melting at 196 – 198 C. C 80.53%, H 5.70%, N 14.20%; m/z = 496.64 1H NMR DMSO d6 400 Mhz : 5ppm 0.96 – 0.99 (t, 3H) 1.75 – 1.84 (m, 2H) 2.62 (s, 3H) 2.89 – 2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18 – 7.92 (m, 14H)

Statistics shows that 152628-02-9 is playing an increasingly important role. we look forward to future research findings about 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5’-bibenzo[d]imidazole.

Reference:
Patent; U AMARNATH, Amarnath; U SURYAKIRAN, Suryakiran; WO2014/27280; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of 1H-imidazole-2-carboxylic acid (0.179) in N,N-dimethylformamide (DMF) (3 mL) was added alanine tert-butyl ester hydrochloride (0.22 g), diisopropylethyl amine (0.27 mL) and HOBT (0.41 g) before cooling to 0 C. and the reaction mixture was then treated with EDC HCl (0.32 g). The cooling bath was removed and the reaction mixture was stirred at ambient temperature for 18 hrs before being diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to afford the sub-title compound as a colourless oil (0.263 g, 73%): 1H NMR 400 MHz CDCl3 1.50 (9H, s), 1.51 (3H, d, J 7.2), 3.70 (1H, m), 7.28 (2H, s), 7.78 (1H, d, J 7.6), 11.49 (1H, br s).

The chemical industry reduces the impact on the environment during synthesis 2-Imidazolecarboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Randle, John C.R.; US2005/267101; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Name is 2-(1H-Imidazol-1-yl)ethanol, 1615-14-1, 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.

General procedure: The following examples were prepared using general procedure described below: A solution of corresponding alcohol (3 equiv) in THF (3 mE) was stirred in an ice-water bath under an atmosphere of Argon. Potassium tert-butoxide (1.0 M, 3 equiv) was added in a single portion and the mixture was stirred at 00 C. for 30 minutes, and then 2-fluoro-5-(4- ((4-(4-(oxetan-3-yl)piperazin-1 -yl)phenyl)amino)-1 ,3,5-tri- azin-2-yl)benzonitrile was added (1 equiv). The mixture was stirred for 2 hr at it Afier the mixture cooled to room temperature, water was added, and mixture evaporated under reduced pressure. Solids were purified via preparative HPEC (5-65% acetonitrile in water, 0.1% trifluoroacetic acid buffer)to yield the final product.

Statistics shows that 2-(1H-Imidazol-1-yl)ethanol is playing an increasingly important role. we look forward to future research findings about 1615-14-1.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1546-79-8, 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. 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, A new synthetic method of this compound is introduced below.

General procedure: The compound 6b (35.1 mg, 50 mumol) was dried by repeated coevaporations with dry MeCN (3 mL) under Ar. The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol), which was dried in vacuo overnight, and a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight, were successively added, and the mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 ¡Á 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 14t, a, c or g as a colorless foam, which was analyzed by 31P NMR (Fig. 2). The 14t, a, c or g thus obtained was dissolved in ethanol (8.0 mL) and a 25% NH3 aqueous solution (40 mL) was added. The mixture was put in a sealed flask and heated at 55 C for 12 h while stirring. The mixture was then cooled to rt, concentrated under reduced pressure to ca. 20 mL The mixture was diluted with a 0.1 M ammonium acetate buffer (pH 7.0) (20 mL) and washed with CHCl3 (4 ¡Á 20 mL). The aqueous layer was then concentrated under reduced pressure. The residue was repeatedly lyophilized from distilled H2O to remove ammonium acetate to give crude the dinucleoside phosphorothioate (15t, a, c or g), which was analyzed by RP-HPLC [Senshu Pak PEGASIL ODS, 4 ¡Á 150 mm, linear gradient of 0-20% MeCN (60 min) in 0.1 M triethylammonium acetate buffer (pH 7.0), 50 C, 0.5 mL/min]. Authentic samples of 15t,a,c,g were synthesized via the solid-phase synthesis using the nucleoside 3?-O-oxazaphospholidines 7t,a,c,g as monomer units [8d].

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; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

To a solution of 4-iodoimidazole (50 g, 258 mmoles) in DMF (500 ml) was added triethyl amine (37.7 ml, 270.6 mmoles) and than triphenylmethyl chloride (69.7 g, 250 mmoles). After stirring at room temperature for 48 hours, the solution was poured into ice water (2.5 L). The solid was filtered and pumped on for several hours to yield the crude compound. Ethyl ether (200 ml) was added to the crude compound and the solution was filtered to yield 4-IODO-1-TRITYL-LH-IMIDAZOLE (104.1, 93%) as a white solid. ME (437)

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

Reference:
Patent; CHIRON CORPORATION; WO2004/96822; (2004); A2;,
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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows., 6160-65-2

Amine (Intermediate A47,16 g, 0.0437 mol) was dissolved in pyridine (200 mL). To this solution was added 1,1′-thiocarbonyldiimidazole (11.68 g, 0.0. 655 mol) and stirred at room temperature overnight under argon. To the reaction mixture was added water (400 mL) and stirred for 1 hr. The resulting solid was collected, washed with water (600 mL) and dried to give 16.9 g (95%) of the title compound, benzimidazolethiol.

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; GARST, Michael, E.; SACHS, George; SHIN, Jai, Moo; WO2004/9583; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1450-93-7, Adding some certain compound to certain chemical reactions, such as: 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), 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 1450-93-7.

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCI, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 oC. A solution 799 mg of NaN02 in 2 mL of water is added dropwise, and the internal temperature is maintained below 5C. The resulting yellow-brown solution is stirred for 30 minutes at 0 o20 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.65 g of 1, 4-diallyl-l, 2,3, 4- tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 oC. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and the dark solid is dried. (E)-6-((lH-imidazol- 2-yl)diazenyl)-l,4-diallyl-l,2,3,4-tetrahydroquinoxaline (2.3g) is used in the next step without further purification.

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 1450-93-7.

Reference:
Patent; NOXELL CORPORATION; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (106 pag.)WO2018/53034; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 84946-20-3 name is 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, 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. 84946-20-3

Example 4; A/-[3-(1-{3-[1-(4-Fluoro-benzyl)-1H-benzoimidazol-2-ylamino]-propyl}-piperidin-4-yl)-phenyl]-acetamide; 2-Chloro-1-(4-fluoro-benzyl)-1H-benzoimidazole (58 mg, 0.22 mmol) and A/-{3-[1-(3-Amino-propyl)-piperidin-4-yl]-phenyl}-acetamide (Example 1 Step 2, 90 mg, 0.33mmol) were mixed in ethanol (1 ml) and heated in the micro wave at 150 C for 2h.The reaction was extracted with dichloromethane and Na2CO3(aq) and the combinedorganic phases was dried over Na2SO4, filtered, and evaporated giving the crudeproduct which was purified by chromatography (silica,dichloromethane/methanol/ammoniac, 9:1:1%) giving the title compound Example 4.1H-NMR (300 MHz, CDCI3); 8 7.5.1 (d, 1H), 7.38 (s, 1H), 7.10-7.31 (m, 6H), 6.92-7.02(m, 4H), 6.79 (d, 1H), 6.61 (br s, 1H), 5.17 (s, 2H), 3.71 (t, 2H), 3.14 (d, 2H), 2.62 (t,2H), 2.48-2.61 (m, 1H), 2.21 (s, 3H) 2.06-2.15 (m, 2H), 1.91-2.00 (m, 2H), 1.65-1.86(m, 4H).LCMS: Rt 3.48 min, m/z 499.6 [M+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-(4-fluorobenzyl)-1H-benzo[d]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; 7TM PHARMA A/S; WO2006/10446; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 3314-30-5 name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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. 3314-30-5

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion using general procedure 3, 3-(2-aminoethyl)-N-benzylbenzamide hydrochloride (380) (171 mg, 0.59 mmol), 1 H-1 ,3-benzodiazole-5-carbaldehyde (129 mg, 0.88 mmol) and DIPEA (102 muIota, 0.59 mmol) in MeOH (5 ml) at room temperature for 72 h, followed by the addition NaB4 (33 mg, 0.88 mmol) gave the title compound (75 mg, 33percent) as a beige solid after purification by basic prepHPLC followed by trituration with DCM. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.16 (s, 1 H), 8.98 (t, J = 5.9 Hz, 1 H), 7.75 (s, 1 H), 7.73 – 7.69 (m, 1 H), 7.54 – 7.39 (m, 2H), 7.39 – 7.34 (m, 2H), 7.32 – 7.29 (m, 4H), 7.26 – 7.20 (m, 1 H), 7.15 – 7.07 (m, 2H), 4.47 (d, J = 6.0 Hz, 2H), 3.93 (s, 2H), 2.86 – 2.77 (m, 4H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Benzo[d]imidazole-2-carbaldehyde, and friends who are interested can also refer to it.

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

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. 570-22-9 name is 1H-Imidazole-4,5-dicarboxylic acid, 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. 570-22-9

Example 29 Diethyl imidazole-4,5-dicarboxylate (46) Imidazole-4,5-dicarboxylic acid (7.55 g, 50.0 mmol) is dissolved in absolute ethyl alcohol (120 mL). The solution was cooled in an ice bath to 0 C. and bubbled dry HCl gas for 1 h. Later, the reaction mixture was refluxed at 80 C. for 7 h during which time all the starting material was consumed. The solvent was removed and the residue that obtained was dissolved in dichloromethane (200 mL) and the organic layer was neutralized with triethylamine. The organic layer was washed with cold water (100 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 5.50 g (52%) of white solid: mp 175-177 C.; 1 H NMR (CDCl3) delta 1.40 (t, 3H), 4.41 (m, 2H), 7.84 (1H, C2 H) and 11.55 (br s, 1H, NH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Imidazole-4,5-dicarboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ICN Pharmaceuticals, Inc.; US6130326; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem