Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, 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 22884-10-2, Computed Properties of C5H6N2O2

A suspension of imidazol-1-ylacetic acid, compound of formula 2 (50g, 0. 396mol) and phosphorous acid (48.7g, 0. 594mol) in sulfolan (180ml) was heated to 75 C for 30 min. The mixture was cooled to 35-40 C and phosphorous trichloride (117ml, 1. 346mol) was gradually introduced while maintaining the temperature between 35-45 C. The mixture was heated to 63-67 C for 3 hours, whereby white solid results. It was then cooled to 0- 5’C and quenched by slow addition of water (500ml) at 0-5 C over a period of 1 hour. The resulting clear solution was heated at 100 C for 3 hours, cooled to ambient temperature and charcoalized. Acetone was added to the charcoalized solution. The mixture was then stirred for 4 hours at 20-25 C and the crystallized product was filtered, washed sequentially with chilled water, acetone and dried to obtain zoledronic acid.

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

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; WO2005/66188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, 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. HPLC of Formula: C7H7N3

Example 38 N-(1H-benzo[d]imidazol-5-yl)-2-(4-(5-chloro-2-propionylphenyl)-5-methoxy-2-oxopyri din-1(2H)-yl)-3-phenylpropanamide 38 Compound 8i (80 mg, 181.86 mumol), 1H-benzo[d]imidazol-5-amine 38a (24.22 mg, 181.86 mumol, prepared by a known method disclosed in “”) and N,N-diisopropylethylamine (70.51 mg, 545.59 mumol) were added to 10 mL of tetrahydrofuran, followed by addition of a solution of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide in ethyl acetate (50%, 231.34 mg, 363.73 mumol). After completion of the addition, the reaction solution was warmed up to 50C, and stirred for 1.5 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was added with 25 mL of saturated sodium bicarbonate solution, and extracted with ethyl acetate (50 mL*2). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by the silica gel column with elution system A to obtain the title compound 38 (75 mg, yield: 74.3%). MS m/z (ESI): 555.5 [M+1] 1H NMR (400 MHz, DMSO-d6) delta 10.84 (s, 1H), 9.05 (s, 1H), 9.14 (s, 1H), 8.27 (s, 1H), 7.79-7.77 (d, 1H), 7.72-7.69 (d, 1H), 7.59-7.52 (m, 2H), 7.41 (s, 1H), 7.34 (s, 1H), 7.30-7.24 (m, 4H), 7.19-7.17 (m, 1H), 6.30 (s, 1H), 6.03-5.99 (m, 1H), 3.52-3.50 (m, 4H), 3.48-3.44 (m, 1H), 2.85-2.75 (m, 2H), 1.25-1.18 (m, 3H).

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

Reference:
Patent; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; YANG, Fanglong; WANG, Weimin; LI, Xiaodong; CHEN, Gang; HE, Feng; TAO, Weikang; (198 pag.)EP3486242; (2019); 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. 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole

The compound of formula I (0.62 g, 1 eq) was added to acetonitrile (10 ml) and stirred well. KOH (0.14 g, 1.1 eq) was added slowly, stirred for about 10 minutes, The title compound of Example 10 was added (II, R = COOCH3) (0.5 g, 1 eq) was slowly added, and after stirring for 3-4 hours, TLC After the reaction was complete, 50% ethanol (30 mL) was added directly, The reaction was refluxed for 6 hours. After the TLC test reaction was complete, the organic solvent was recovered under reduced pressure, The remaining solution was added dropwise with hydrochloric acid (1: 1) to pH neutral. There are solid precipitation, filtration, washing, extraction of telmisartan crude, Recrystallization of telmisartan (yield 75.1%), liquid purity greater than 98%.

According to the analysis of related databases, 152628-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Specialization Pharmaceutical Technology Co., Ltd.; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shandong Tefaman Pharmaceutical Co., Ltd.; Wu Mingjun; Li Jianfeng; Chen Weiming; Tian Guanghui; Zhu Fuqiang; Suo Jin; Shen Jingshan; (14 pag.)CN104768936; (2017); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-21-0, A common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.

To a solution of 5-bromo-1-methyl-imidazole (18.8 g, 117 mmol) in dichloromethane (50 mL) was added dropwise ethylmagnesium bromide (3 M in Et2O, 38.9 mL, 117 mmol). After stirring at room temperature for 30 min, the reaction mixture was cooled down to 0C with an ice-brine bath and N-methoxy-N-methylthiophene-3-carboxamide (20.0 g, 117 mmol) was added dropwise. The mixture was stirred for 5.5h at room temperature. The mixture was worked-up by addition of water (400 mL), then acidified with aq. HCI (1 M) until pH = 7. After extraction with dichloromethane (3 x 100 mL), the organic layers were washed with water (2 x 100 mL) then dried over MgSO4 and concentrated in vacuo. Purification of the residue on silica gel afforded (1-methyl-1H-imidazol-5-yl)(2-thienyl)methanone [10.2 g, yield 36% ; HPLC/MS : m/z = 193 (M+H) ; logP(HcooH) = 0.52].

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; BAYER CROPSCIENCE SA; WO2009/130193; (2009); 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. 4499-07-4, name is 2-(1H-Benzo[d]imidazol-2-yl)ethanamine dihydrochloride, A new synthetic method of this compound is introduced below., Product Details of 4499-07-4

To a solution of benzimidazole ethylene amine dihydrochloride (100 mg, 0.43 mmol), 3,4-dimethylphenoxyacetic acid (77 mg, 0.43 mmol), and BOP reagent (190 mg, 0.43 mmol) in acetonitrile (5 mL) was added triethylamine (0.23 mL, 1.72 mmol). After stirring at room temperature overnight, the solvent was removed under vacuum. The residue was taken up with water and saturated sodium bicarbonate (20 mL), extracted with dichloromethane (30 mL x 2), dried and removed the solvent. The crude mixture was purified by using Gilson HPLC to give white solid 5 as a TFA salt (170 mg) at 93 % yield. MUX LC/MS (10-99%) M+1/Z 324.163 retention time 2.62 min ; 1H NMR (DMSO) 8 2.12 (s, 3H), 8 2.15 (s, 3H), 8 2.99 (t, 2H, J = 5.88 Hz), 8 3.59 (m, 2H), 8 4.40 (s, 2H), 8 6.64 (dd, 1H, J = 2 Hz, 6.5 Hz), 8 6.75 (d, 1H, J = 1.8 Hz), 8 6.98 (8, 1H, J = 6.6 Hz), 8 7.12 (m, 2H), 7.40 (d, 1H, J = 5.76 Hz), 7.53 (m, 1H), 8.30 (t, 1H, J = 4.56 Hz), 12.24 (s, 1H) ; 13C NMR (DMSO) 8 18.4, 8 19. 57, 8 28.58, 8 36.74, 8 67.07, 8 110.8, 8 111.58, 8 116.13, 8 118.12, 8 120.86, 8 121.52, 8 128. 70, 8 130.12, 8 134.21, 8 137.25, 8 143. 24, 8 152. 74, 8 155.73, 8 167. 85.

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; VERTEX PHARMACEUTICALS, INCORPORATED; WO2005/42497; (2005); 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. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromo-1,2-dimethyl-1H-imidazole

To a 50-mL round-bottom flask containing a solution of 5-bromo-1,2-dimethyl-1H-imidazole (440 mg, 2.51 mmol, Intermediate 24, step a) and THF (20 mL) under nitrogen was added isopropylmagnesium chloride in THF (2.0 M, 1.2 mL, 2.4 mmol) dropwise. The mixture was stirred for 0.5 hours at room temperature, and a solution of 4-chloro-N-methoxy-N-methylbenzamide (500 mg, 2.50 mmol, Intermediate 18, step a) in THF (5 mL) was introduced. After stirring for 7.5 hours at room temperature, the reaction was quenched by addition of 10 mL of EtOH, and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 50% EtOAc in petroleum, 0-10% MeOH in CH2Cl2) to give the title compound as a white solid.

According to the analysis of related databases, 24134-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 334893-99-1, The chemical industry reduces the impact on the environment during synthesis 334893-99-1, name is (5-Chloro-1-methyl-1H-imidazol-2-yl)methanol, I believe this compound will play a more active role in future production and life.

A Dess-Martin reagent (1.04 g, 2.46 mmol) was added to a solution of (5-chloro-1-methyl-1H-imidazol-2-yl)methanol (0.300 g, 2.05 mmol) in dichloromethane (20.0 mL) at 0 C. The reaction liquid was stirred at room temperature for 4 hours. The reaction liquid was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, n-hexane/ethyl acetate) to obtain 5-chloro-1-methyl-1H-imidazole-2-carbaldehyde (0.289 g, 2.00 mmol, 98%) as a white solid. (0157) 1H-NMR (400 MHz, CDCl3) delta: 3.97 (3H, s), 7.24 (1H, s), 9.70 (1H, s).

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-Chloro-1-methyl-1H-imidazol-2-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Toray Industries, Inc.; Osada, Yuji; Izumimoto, Naoki; Morita, Yasuhiro; Udagawa, Shuji; Iseki, Katsuhiko; Miyoshi, Tomoya; Iwano, Shunsuke; (38 pag.)US2018/72701; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 10364-94-0, These common heterocyclic compound, 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, 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.

General procedure: In a round bottomed flask 0.01 mol (1.36 g) phenyl acetic acid and 0.012 mol (1.94 g) of CDI were added. The reaction mixture was mixed and grinded with a spatula. CO2 gas starts releasing with increase in temperature and solid reaction mixture was turned to pale yellow liquid within 5 min. 0.001 mol (0.1 g) Imidazole. hydrochloride, 0.01 mol (0.87 g) of morpholine, and 1 mL of water were added to it. The reaction mixture was kept at room temperature for another 10 min. Dilute hydrochloride solution was added to it and the aqueous layer was washed with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to give pure product.

Statistics shows that (1H-Imidazol-1-yl)(phenyl)methanone is playing an increasingly important role. we look forward to future research findings about 10364-94-0.

Reference:
Article; Verma, Sanjeev K.; Ghorpade, Ramarao; Pratap, Ajay; Kaushik; Tetrahedron Letters; vol. 53; 19; (2012); p. 2373 – 2376;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2963-77-1, 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. 2963-77-1 name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, 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.

To a solution of stannous chloride 1.6 g, (8.4 mmol) in 30 mL water was added 1.75g (8.4 mmol) of PBA in 30mL ethanol. The reaction mixture was stirred at room temperature for 30 min and then a solution of BPE (2 g, 8.4 mmol in 30 mL water) was added to mixture and heated at 100C for 14 h. The progress of reaction was controlled with TLC (DMF/water: 50/50). At the end of reaction, the reaction mixture was cooled, diluted with ethanol (40 mL), filtered and washed with ethanol and then with DMF to obtain a red precipitate. Yield: 85%, m.p. : 230C; m.f.: C28H26N6SnCl2. UV-vis (DMSO); max (nm): 280, 310, 430. IR (KBr, max, cm-1): 3443 (m), 3338 (m), 3224(m), 1601 (s), 1567 (s), 1497 (s), 1411 (m), 1320 (s), 1236 (s), 1168 (s), 1110 (s), 1069 (s), 849 (s), 744 (m), 607 (m) 498 (m), 434 (m).

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

Reference:
Article; Aroua, Lotfi M.; Asian Journal of Chemistry; vol. 32; 6; (2020); p. 1266 – 1272;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 17334-08-6, name is (1-Methyl-1H-imidazol-2-yl)methanol, 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. Safety of (1-Methyl-1H-imidazol-2-yl)methanol

Synthesis of 2-(Chloromethyl)-1-methyl-1H-imidazole Hydrochloride (BB7) To a solution of (BB6) (35.5 g, 316.96 mmol) in DCM (1500 mL) was added SOCl2 (330 mL, 4436 mmol) at 0 C. The reaction was warmed to ambient temperature and stirred for 5 h. The reaction mixture was concentrated, the residue was washed with DCM (2*500 mL), followed by Et2O (2*200 mL) to obtain (BB7) (50 g, 95%) as an off-white solid. Rf: 0.4 (EtOAc). 1H NMR (400 MHz, DMSO-d6): delta 7.76 (1H, app d), 7.70 (1H, app d), 5.17 (2H, s), 3.87 (3H, s); ink 131 (MH)+.

The synthetic route of (1-Methyl-1H-imidazol-2-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; ST GEORGE’S HOSPITAL MEDICAL SCHOOL; US2012/322722; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem