Month: November 2020

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

288-32-4, 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. 288-32-4, name is 1H-Imidazole, A new synthetic method of this compound is introduced below.

General procedure: A 25 mL flask with a magnetic stirring bar was charged with CuI(9.6 mg, 0.05 mmol), metformin (0.1 mmol), Cs2CO3 (652 mg,2.0 mmol), imidazole (1.0 mmol), an aryl halide (1.1 mmol), andDMF (5 mL). The mixture was stirred for 10 min at room temperature,and then heated to 110?C for the appropriate amount of time(see Table 2). The progress of the reaction was monitored by TLC.After completion of the reaction, the mixture was extracted with EtOAc (5 1 mL) and the organic phase separated and evaporated. Further purification by column chromatography gave the desired coupled product.

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; Ghorbani-Vaghei, Ramin; Hemmati, Saba; Veisi, Hojat; Tetrahedron Letters; vol. 54; 52; (2013); p. 7095 – 7099;,
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. 57090-88-7, name is 1H-Imidazole-4-carbonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. 57090-88-7

General procedure: A solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

The synthetic route of 57090-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, Adding a certain compound to certain chemical reactions, such as: 39021-62-0, name is 1-Methyl-1H-imidazole-5-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 39021-62-0.

Step 1 A solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.46 g, 13.26 mmol), (R)-2-methylpropane-2-sulfinamide (2.893 g, 23.87 mmol), and tetraethoxytitanium (10.89 g, 47.73 mmol) in THF (100 mL) was heated to 65 C. for 12 h. The reaction was cooled and poured onto water. The solids were filtered off, and the filtrate was extracted with EtOAc. The layers were separated, and the organic layer was concentrated. The resulting residue was purified by SiO2 eluting with a DCM/MeOH gradient (1.5 to 2% MeOH) to afford 1.444 g (51.1%) of (R,E)-2-methyl-N-((1-methyl-1H-imidazol-5-yl)methylene)propane-2-sulfinamide (128).

According to the analysis of related databases, 39021-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem