Month: November 2020

16265-04-6,Some common heterocyclic compound, 16265-04-6, name is 2-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 ¡Á 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1H-imidazole, its application will become more common.

Reference:
Article; Liang, Yufan; Zhang, Xiaheng; MacMillan, David W. C.; Nature; vol. 559; 7712; (2018); p. 83 – 88;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

67085-11-4, These common heterocyclic compound, 67085-11-4, name is 4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol, 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.

Take 5kg of 1-(2-hydroxy-4-(4-chlorophenyl)butyl)-1H-imidazole and dissolve it sufficiently in 35kg of methylene chloride. 5kg of thionyl chloride was added dropwise at a rate of 1.5ml/s at 20C, and the temperature was slowly raised to 32C and the reaction was incubated for 1 hour. Then reflux at 60 C for 1 hour, slowly cooled to 15 C to obtain the reaction solution; In the reaction solution, 10 C. water was added at a rate of 0.5 ml/s with stirring, and the volume ratio of the reaction solution to water was 0.005:1. Anhydrous sodium carbonate was further added at 1.0 to 1.5 kg/L. After suction filtration, the solid was discarded, the liquid was concentrated at 55 C. until no dichloromethane was distilled off, and dried to obtain 1-(2-chloro-4-(4-chlorophenyl)butyl)-1-hydro-imidazole. The purity is 99.17%. The 1-(2-chloro-4-(4-chlorophenyl)butyl)-1H-imidazole was used as a raw material in Examples 1 to 5.

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 67085-11-4.

Reference:
Patent; Zhuzhou Qianjin Pharmaceutical Co., Ltd.; Peng Kaifeng; Wen Fengqiu; Bai Lu; Li Sanxin; Gong Yun; Li Fujun; (12 pag.)CN105198816; (2018); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

934-22-5, 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. 934-22-5 name is 6-Aminobenzimidazole, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminobenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 288-32-4, name is 1H-Imidazole, I believe this compound will play a more active role in future production and life. 288-32-4

To a solution of imidazole 5 (2 g, 30 mmol) and sodium acetate(22 g) in 50 mL glacial acetic acid, was added a solution of Br2(4.6 mL, 90 mmol) in acetic acid (10 mL) within 30 min. The reactionmixture was stirred at room temperature for 2 h and thenpoured into 50 mL ice water. The resulting precipitate was filteredand washed with water to afford 9 as white solid (5.4 g, 59% yield);mp: 221-222 C (lit. mp 218-221 C) [42].

The chemical industry reduces the impact on the environment during synthesis 288-32-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shirvani, Pouria; Fassihi, Afshin; Saghaie, Lotfollah; Van Belle, Siska; Debyser, Zeger; Christ, Frauke; Journal of Molecular Structure; vol. 1202; (2020);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, Name is 1-Methyl-1H-imidazole-2(3H)-thione, 60-56-0, 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.

A solution of 0.139 g (1.22 mmol) of imidazole 2 in 2 mL of DMF and 0.084 g (0.66 mmol) of K2CO3 were added to a solution of 0.298 g (1.22 mmol) of thiaselenole 1 in 3 mL of DMF. The reaction mixture was stirred at room temperature for 2 h, diluted with water (50 mL), and the reaction products were extracted with CCl4 (3 ¡Á 5 mL). The extract was washed with water (3 ¡Á 5 mL), dried over Na2SO4, and the solvent was removed in a vacuum. Yield 0.270 g (80%), brown oily substance. 1H NMR spectrum (CDCl3), delta, ppm: 3.08 d.d (1, Se, 2J12.1, 3J 7.8 Hz), 3.43 d.d (1, Se, 2J 12.1, 3J2.6 Hz), 3.57 s (3, N3), 4.80 d.d (1, SS, 3J7.8, 3J 2.6 Hz), 6.24 d (1, =S, 3J 9.9 Hz), 6.34 d(1, SeCH=, 3J 9.9, 2JSe,H 51.2 Hz), 6.89 d (1, 5, 3J1.3 Hz), 6.97 d (1, 4, 3J 1.3 Hz). 13C NMR spectrum(CDCl3), delta, ppm: 24.58 (2Se, 1JC,Se 64.0 Hz), 33.55(N3), 47.27 (SS), 109.61 (=Se, 1JSe,C 116.6 Hz),117.86 (=S), 122.85 (5), 129.49 (4), 137.56 (C2).77Se NMR spectrum (CDCl3), delta, ppm: 193.3. 15N NMRspectrum (CDCl3), delta, ppm: -212.0 (N1), -109.7 (N3).Mass spectrum, m/z (Irel, %): 278 (71) [M]+, 219 (10),197 (16), 164 (57), 151 (15), 139 (100), 114 (95), 84(78), 60 (49), 42 (54). Found, %: C 34.47; H 3.54; N9.92; S 23.00. C8H10N2S2Se. Calculated, %: C 34.65;H 3.64; N 10.10; S 23.13.

Statistics shows that 1-Methyl-1H-imidazole-2(3H)-thione is playing an increasingly important role. we look forward to future research findings about 60-56-0.

Reference:
Article; Amosova; Filippov; Potapov; Makhaeva; Albanov; Russian Journal of Organic Chemistry; vol. 54; 11; (2018); p. 1697 – 1701; Zh. Org. Khim.; vol. 54; 11; (2018); p. 1682 – 1686;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate, 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. 23785-21-9

Add 100 g (0.714 mol, 1.0 eq) of imidazole-4-ethyl formate and 1.4 L of dichloromethane to a 2L four-mouth bottle equipped with a mechanical stirring and a thermometer to form a suspension; add 219 g(0.787 mol, 1.1 eq) of triphenylchloromethane and 79.4 g (0.787 mol, 1.1 eq) of triethylamine to the suspension, slowly heat to 2530 C., the liquid turns clear. Continue to stir for 20 h to the reaction finish. Add 200 mL water and stir 30 mins, then standing for layered. Separate the organic phase and extract the water phase by 100 mL dichloromethane. Combine the organic phase and wash it once by 200 mL water. Concentrate the organic phase to get alight yellow oil; then 500 mL diethyl ether is added, a great amount of white solids are generated when the mixed solution is stirred; filter and dry to obtain 269 g 1-trityl -1H-imidazole-4-ethyl formate, with a yield of 98% and a purity of 90% (HPLC).

Statistics shows that 23785-21-9 is playing an increasingly important role. we look forward to future research findings about Ethyl 1H-imidazole-4-carboxylate.

Reference:
Patent; TIANJIN WEIJIE PHARMACEUTICAL CO., LTD; SONG, Honghai; SUN, Zhicun; HUANG, Haiping; ZHANG, Chao; (5 pag.)US2016/272594; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

(Reference Example 18) Synthesis of 1-propyl-1H-imidazole: Sodium hydride (55%, 0.966 g, 22.1 mmol) was added to a solution of imidazole (1.37 g, 20.1 mmol) in tetrahydrofuran (50.0 mL) at room temperature. The reaction liquid was stirred at the same temperature for 1 hour, and then, 1-bromopropane (5.48 mL, 60.3 mmol) was added at room temperature. The reaction liquid was stirred at the same temperature for 16 hours. The reaction liquid was filtered through Celite and washed with tetrahydrofuran, and then the filtrate and the washing solution were concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, chloroform/methanol) to obtain 1-propylimidazole (2.07 g, 18.8 mmol, 93%) as a colorless oil. 1H-NMR (400 MHz, CDCl3) delta: 0.93 (3H, t, J=7.2 Hz), 1.81 (2H, td, J=7.2, 14.4 Hz), 3.90 (2H, t, J=7.2 Hz), 6.91 (1H, s), 7.06 (1H, s), 7.46 (1H, s).

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Toray Industries, Inc.; ARAI Tadamasa; MORITA Yasuhiro; UDAGAWA Shuji; ISEKI Katsuhiko; IZUMIMOTO Naoki; (95 pag.)EP3263565; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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