Tag: M.W=100-200

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

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

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

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

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

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

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

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

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

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