Imidazoles-derivatives

51605-32-4, 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. 51605-32-4 name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

Using a modified procedure of Sreedhar. (Reference: Sreedhar, B., Synthesis, 795 (2008)). To a suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (0.530 g, 3.44 mmol) and (3-chloro-2-fluorophenyl)boronic acid (0.500 g, 2.87 mmol) in MeOH (5.74 mL) was added cuprous oxide (0.041 g, 0.287 mmol). The resulting purple suspension was stirred vigorously under an atmosphere of air (drying tube used). After 20 h, thereaction mixture was filtered to remove the solids and the clear blue filtrate was concentrated to give a blue solid. The blue solid was suspended in DCM and filtered to remove the solids and the blue filtrate was concentrated to give a pale blue solid weighing 0.187 g. Purification by normal phase chromatography gave ethyl 1-(3-chloro-2- fluorophenyl)-4-methyl- 1H-imidazole-5-carboxylate (0.0187 g, 2percent) as a clear, colorlessresidue and ethyl 1 -(3 -chloro-2-fluorophenyl)-5 -methyl- 1H-imidazole-4-carboxylate (Intermediate 24A) (0.0079 g, 1percent) as a clear, colorless residue. MS(ESI) m/z: 283.1 (M+H)

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-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 71759-89-2, 71759-89-2

At 0 C., to a solution of 4-iodo-1H-imidazole (5 g, 25.8 mmol) in DMF (100 mL) was added triethylamine (3.13 g, 30.9 mmol) slowly. After stirring for additional 10 min at 0 C., the reaction mixture was added by TrtCl (7.17 g, 25.7 mmol). The resulting solution was then stirred at room temperature for 16 h. The reaction mixture was poured into 1 L water. A white solid precipitated out and were collected by filtration. The solid was rinsed with MeOH (50 mL¡Á2) and Et2O (50 mL¡Á3), and then dried in vacuo to yield 4-iodo-1-(triphenylmethyl)-1H-imidazole as white solid (10.4 g, 92%).

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

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; (167 pag.)US2016/75711; (2016); A1;,
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.

4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71%) was obtained as a white solid.

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; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

3314-30-5, Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 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 to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-[(5-methylpyrimidin-2-yl)methyl]- 1 ,3-thiazole-4-carboxamide dihydrochloride (197) (223 mg, 0.52 mmol), 1 H-benzimidazole-2-carbaldehyde (99 mg, 0.68 mmol), DIPEA (0.363 ml, 2.09 mmol) and MgSQ (400 mg) in MeOH (6 ml) at room temperature for 24 h, followed by addition of NaBH4 (30 mg, 0.78 mmol) gave the title compound (120 mg, 52percent) as a white solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.21 (s, 1 H), 8.72 (t, J = 5.8 Hz, 1 H), 8.63 – 8.57 (m, 2H), 7.50 (s, 1 H), 7.14 (dd, J = 6.0, 2.7 Hz, 2H), 4.61 – 4.56 (m, 2H), 3.98 (s, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.95 (t, J = 6.3 Hz, 2H), 2.75 (s, 1 H), 2.26 (s, 3H) HPLCMS (Method C): [m/z]: 442 [M+H]+

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-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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

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 26576-46-5 as follows. 26576-46-5

Dispersion synergist SYN-8; Formation of the dispersion synergist SYN-8 was accomplished by diazotation of compound 11 and subsequent coupling with compound 3 [Show Image] 18.1 g (0.1 mol) of compound 11 in 300 mL water was dissolved by adding 10 mL (0.1 mol) of a 29% sodiumhydroxide-solution. 8.97 g (0.13 mol) of sodiumnitrite was added and the colourless solution was dropwise added to cooled concentrated hydrochloric acid (29.98 mL; 0.36 mol). The diazonium-salt was kept at a temperature between 0 and 5 C. After 15 minutes the excess of nitrite was neutralized by adding 3.0 g (0.03 mol) of sulfamic acid and a pH of 7 was obtained by adding 25.2 g (0.3 mol) of sodiumcarbonate. While the diazionium-salt was made, 23.3 g (0.1 mol) of compound 3 was dissolved in a mixture of 500 mL methanol and 10.0 mL (0.1 mol) 29 % sodiumhydroxide-solution. This solution was dropped into the diazonium-salt solution and a yellow suspension is immediately formed. The temperature was maintained between 0 and 5 C for about 3 hours and the yellow product was filtered and washed with methanol. The yield was 70 %.

According to the analysis of related databases, 26576-46-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agfa Graphics N.V.; EP1790697; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

583-39-1, A common compound: 583-39-1, name is 2-Mercaptobenzimidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A mixture of 1H-benzo[d]imidazole-2(3H)-thione (III, 21 mg, 0.2 mmol) and [RuII(eta6-p-cymene)(PPh3)(CH3CN)Cl]PF6 (5, 144 mg, 0.2 mmol) in CH2Cl2 (20 mL) was stirred for 3 h at room temperature. The solvent was concentrated to a small amount (ca. 3 mL) and the product was precipitated by addition of pentane (ca. 20 mL). The orange yellow powder was filtered, washed with pentane (2 ¡Á 5 mL) and dried in vacuo. Yield: 146 mg (88%), m.p. 200 C (decomp.). Elemental analysis (%) calcd. for C35H35ClF6N2P2RuS*0.5CH2Cl2: C 48.97, H 4.17, N 3.22, S 3.68, found: C 49.02, H 4.38, N 3.29, S 3.74. 1H-NMR (CDCl3): delta = 11.46 (s, 2H, NH),7.58-7.62 (m, 6 H, PPh3), 7.34-7.37 (m, 10H, PPh3/Ar-thione), 7.24-7.27 (m, 3H, PPh3), 5.47 (d, J = 6 Hz, 1 H, H-Ar), 5.31 (d, J = 6 Hz, 1 H, H-Ar), 5.21 (d, J = 6 Hz, 1 H, H-Ar), 5.06 (d, J = 6 Hz, 1 H, H-Ar), 2.81-2.89 (m, 1 H,CH(CH3)2), 1.90 (s, 3 H, CH3), 1.18 (d, J = 7 Hz, 3H, CH(CH3)2), 1.16 (d, J = 7 Hz, 3H, CH(CH3)2) ppm. 13C{1H}-NMR (CDCl3): delta = 163.8 (C=S), 134.1 (C-PPh3), 132.0 (C-PPh3), 131.6 (C-Arthione), 131.1 (C-Arthione), 130.8 (C-PPh3), 128.4 (C-PPh3), 124.6 (C-Arthione), 116.5 (C-Ar), 111.7 (C-Arthione), 101.1 (C-Ar), 92.0 (d, J = 2 Hz, C-Ar), 91.3 (d, J = 4 Hz, C-Ar), 90.0 (d, J = 2 Hz, C-Ar), 89.0 (d,J = 4 Hz, C-Ar), 30.5 (CH(CH3)2), 22.5(CH(CH3)2), 21.4 (CH(CH3)2), 17.6 (CH3) ppm. 31P{1H}-NMR(CDCl3): delta = 29.5 (s, PPh3), -144.2 (sept, PF6) ppm.

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, 2-Mercaptobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hanif, Muhammad; Nawaz, Muhammad Azhar Hayat; Babak, Maria V.; Iqbal, Jamshed; Roller, Alexander; Keppler, Bernhard K.; Hartinger, Christian G.; Molecules; vol. 19; 6; (2014); p. 8080 – 8092;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Adding some certain compound to certain chemical reactions, such as: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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 1615-14-1.

To a stirring mixture of the methyl 2-(4-hydroxyphenyl)acetate (1.4 g, 1 EQ) and 2-(lH-imidazol-l-yl)ethanol (1.0 g) in THF (0.5 mL, 0.5 M) at 0 0C was added PPh3 (2.9 g). To this mixture was added dropwise DIAD (2.2 mL) over 10 min. The reaction mixture was warmed to ambient temperature overnight. A normal aqueous workup with water and EtOAc was followed. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified via silica gel chromatography to give methyl 2-(4-(2- (lH-imidazol-l-yl)ethoxy)phenyl)acetate. Method[l], MS(ESI) 261.1, Retention time = 0.782 min.

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 1615-14-1.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 52099-72-6 as follows. 52099-72-6

1-Isopropenyl-2-benzimidazolone (4.0 g, 0.023 mol), Intermediate I (9.8 g, 0.03 mol), 45% NaOH (12¡¤5 g, 0¡¤14 mol), was added to a 250 ml reaction flask. 25 ml of propanol and 110 ml of water were heated to 75 degrees and stirred for 2 hours. The reaction was completed, concentrated hydrochloric acid was added to adjust PHI, stirring was continued for 1 h, and the solid obtained by filtration was cooled.Adding to DCM and water, adjusting the pH to alkaline, separating the organic layer, drying and concentrating, and concentrating the obtained product by recrystallization from acetone to obtain the finished product of Flibanserin.

According to the analysis of related databases, 52099-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Langsheng Pharmaceutical Co., Ltd.; Li Zhimin; Chen Yuhua; Zhao Yujiao; Chen Weiqiang; Zhao Zhirong; Lu Zhijun; (7 pag.)CN109384680; (2019); A;,
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. 60-56-0 name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. 60-56-0

EXAMPLE 4 1-methyl-2-[3-[(p-isobutyloxycarbonyl)-phenoxy]-2-hydroxy-propylthio]-imidazole hydrochloride The suspension of 5.73 g (50 mmoles) of 1-methyl-2-mercapto-imidazole in absolute ethanol (100 ml) is added with 2,6-lutidine in catalytic amount and there is dropwise added the solution of isobutyl p-(2,3-epoxy)-propyloxybenzoate (12.5 g; 50 mmoles) in absolute ethanol (50 mmoles) at room temperature under stirring.The mixture is heated to reflux for 6 hours. The solvent is evaporated under vacuum, the residue is taken with ethyl acetate and washed with aqueous saturated solution of sodium bicarbonate and with water. The mixture is made anhydrous over anhydrous sodium sulfate and concentrated to an oil. The lutidine is completely removed by evaporation under vacuum. The product, dissolved in acetone, is treated with an excess of 37% aqueous hydrochloric acid and maintained under stirring until the salification is completed.The mixture is concentrated to dryness under vacuum with subsequent additions of toluene/ethanol, the solid is comminuted with ethyl ether/hexane and is crystallized from a mixture of acetone/ethyl acetate.The product is obtained with a yield of 64% and has melting point 104-108oC.. By repeating the operating method of example 4 the following derivatives are prepared:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-imidazole-2(3H)-thione, and friends who are interested can also refer to it.

Reference:
Patent; PIERREL S.p.A.; EP520552; (1992); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

26576-46-5, These common heterocyclic compound, 26576-46-5, name is 5-Acetoacetlamino benzimdazolone, 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.

244kg 1,2-bis(o-aminophenoxy)ethane, 600kg mass percentage concentration of 30% hydrochloric acid and 1500kg water was stirred and beaten. Add 2000kg ice to cool to 5 deg.C. Add 363kg mass percentage concentration of 40% sodium nitrite to start diazotization. At diazotization end, eliminate excess sodium nitrite, to give a diazonium salt solution.280kg 5-aminoacetylacetylbenzimidazolone, dissolved in 250kg mass percentage concentration of 30% aqueous sodium hydroxide and 3000kg of water. Adjust the temperature to 5 deg.C. Add in a fine stream 1500 mass concentration of 10% diluted acetic acid until the acid precipitation end, pH value of 7, to obtain a coupling solution.The diazonium salt solution was slowly added over 3 hours to the coupling solution to undergo reaction. The pH during the coupling process was maintained using 850kg 30% concentration sodium bicarbonate to control the system pH to 7. The coupling ends. Temperature was raised to 90 deg. C, and maintained at this temperature for 2 hours, filtered to give the crude pigment filter cake. 1660kg solid content of 40% of the crude pigment filter cake was added to 4000kgDMF slurried in good stirring and heated to reflux, 5-8 hours of incubation, washing, drying at 85-90 deg.C under pulverized to obtain 665kg products.

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 26576-46-5.

Reference:
Patent; Shangyu?City Xinli Chemical Co.,Ltd.; Chen, Jianxin; Ni, Yuebiao; Zhang, Lixin; Fang, Biao; (15 pag.)CN105670340; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem