Tag: M.W=100-200

Synthetic Route of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 suspension of bis(2-chloroethyl)ammonium chloride (1.43 g, 8.01 mmol) in dichloromethane (DCM) phosphorus trichloride (0.32 ml, 3.64 mmol) was added at rt followed by addition of TEA (3.05 ml, 21.84 mmol). The reaction mixture was stirred at rt for 30 minutes and then N-methyl 2-nitroimidazolyl methanol (0.474 g, 3.31 mmol) in DME was added. After stirring for 0.5 hour, the reaction mixture was cooled to -2O0C and tert- butyl hydroperoxide (0.7 ml, 3.82 mmol, 5.5 M in Decane) was added. The reaction mixture was warmed to rt over a period of one hour, and poured into 10% aqueous HCl. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic solution was dried with MgSO4 and concentrated to yield a residue which was purified by flash chromatography with 6-12% methanol in DCM yielding 6.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THRESHOLD PHARMACEUTICALS, INC.; WO2007/2931; (2007); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 60-56-0, These common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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: A mixture of N-(naphthalen-1-yl)propanamide (1.50 mmol,0.35 g) and mercapto derivatives (1.50 mmol) were dissolved in acetone (15 ml). For catalytic purposes, potassium carbonate(1.50 mmol, 0.21 g) was added to the round bottom flask. After 2 h, the reaction was monitored by TLC. Ultimately the solvent was vanished to dryness, the solid was filtered and washed with water. The final products were recrystallized from ethanol.

The synthetic route of 60-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Evren, Asaf E.; Yurttas, Leyla; Y?lmaz-Cankilic, Meral; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 195; 2; (2020); p. 158 – 164;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 6775-40-2, 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. 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution ofaldehyde (1 mmol), amine (1 mmol), CCl3CN (2 mmol) in PEG-400 (5mL) at 0 oC, a solution of H2O2 (30%) (3mmol)was added drop wise. Then the reaction mixture was stirred at room temperature for 8-12 h. After completion ofthe reaction (monitored by TLC), the reaction mixture was poured into ice water (50 mL). The solid obtained wasfiltered, washed with water and crude product was purified by column chromatography (silica gel, 60-120 mesh)using hexane/ethylacetate (6:4) as eluent.

The chemical industry reduces the impact on the environment during synthesis 5-Phenyl-1H-imidazol-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi; Arkivoc; vol. 2019; 6; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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 stirring solution of 1,1?-thiocarbonyldiimidazole (1.2 equiv) in5 mL of DMF at 50 C was added a solution of TEA (1 equiv) and amine5 (1 equiv) in DMF dropwise. The resulting solution stirred at roomtemperature for 1-24 h and was monitored by TLC. The resulting crudesolution of the isothiocyanate was used in the next step without purification.

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

Reference:
Article; Chapa, Jorge De La; Valdez, Matthew; Ruiz, Franscisco; Gonzales, Keith; Mitchell, Wes; McHardy, Stanton F.; Hart, Matthew; Polusani, Srikanth R.; Gonzales, Cara B.; Bioorganic and Medicinal Chemistry; vol. 27; 1; (2019); p. 208 – 215;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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 13 4,5-Bis(ethoxycarbonyl)imidazole A mixture of 4.0 g (25.6 mmols) of imidazole-4,5-dicarboxylic acid, 600 ml of ethanol and 16 ml of conc. sulfuric acid was heated under reflux for 7 hours. After cooling to 0 C., the mixture was neutralized with a 2 normal aqueous sodium hydroxide solution. The solvent was evaporated under reduced pressure, and then water was added to the residue followed by extraction of the solution with chloroform. The chloroform layer was washed with an aqueous saturated sodium bicarbonate solution and then with an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was dried to afford 2.5 g (yield: 46%) of the title compound. NMR (CDCl3) delta (ppm): 7.83(1H, s), 7.26(1H, s), 4.41 (4H, q, J=7.2 Hz), 1.38(6H, t, J=7.2 Hz)

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd.; US5053408; (1991); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 35445-32-0, 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. 35445-32-0 name is Ethyl 1,4-dimethyl-1H-imidazole-5-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.

Add NaOH (0.451 g, 10.7 mmol) to a solution of ethyl 3,5-dimethylimidazole-4- carboxylate (1.00 g, 5.35 mmol) in EtOH (5 mL) and water (5 mL). Stir the reaction mixture at 60 ¡ãC for 1 hr. Concentrate the solution to give the title compound (0.960 g, 99.6percent) as a yellow solid. LC/MS (mlz): 141 (M-21).

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

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; HU, Zhilong; LIU, Lianzhu; MA, Tianwei; ZENG, Mi; ZHANG, Haizhen; (37 pag.)WO2018/14800; (2018); 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. 4856-97-7, name is (1H-Benzoimidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8N2O

Starting from the o-phenylenediamine compound (1.0equiv) and glycolic acid (2.0equiv), the reaction was refluxed in the presence of a 4.0 mol/L aqueous hydrochloric acid solution, and the TLC was traced until the reaction of the starting material was complete, and the reaction solution was cooled. To room temperature,Adjusting the pH to 7 with 20% NaOH, standing to precipitate a solid, suction filtration, and drying to obtain compound 5; transferring compound 5 to a round bottom flask,Add NaOH aqueous solution,KMnO4 (2.5 equiv) was added in portions at 80 C with stirring, and the reaction was continued after the addition.After all the raw materials were completely reacted, the reaction solution was cooled to room temperature, and the filtrate was filtered by suction.Adjust the pH to neutral with 20% aqueous HCl solution to precipitate a solid.Drying by suction filtration to obtain compound 6;Compound 6 with DMF(1.0equiv) dissolved, then added 1-hydroxybenzotriazole (HOBt, 1.1equiv)And 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 1.1 equiv),The reaction was stirred at room temperature for 30 min, and then compound 4 (1.1 equiv) was added to the reaction solution.Continue to stir the reaction,The TLC traces to the completion of the reaction of the starting material, and the reaction solution is poured into ice water.It was then extracted with ethyl acetate and the organic layer was evaporated.The crude product was purified by column chromatography to give the allyl intermediates Sb.

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 4856-97-7.

Reference:
Patent; Sun Yat-sen University; Qiu Liqin; Jiang Xiaoding; (74 pag.)CN109336887; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 312-73-2,Some common heterocyclic compound, 312-73-2, name is 2-(Trifluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H5F3N2, 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.

G. Synthesis of Compounds 46 and 47A stirred mixture of 2-Trifluoromethyl-I H-benzoimidazole (4.92g, 26.4 mmol), 4-fluorobenaldehyde (3.1 mL, 29.1 mmol), and K2CO3 (4.37g, 31.7 mmol) in DMF (50 mL) was heated to 150 0C for 16 h. After being cooled to room temperature, the reaction mixture was partitioned between H2O and EtOAC. After usual workup, the crude product was purified by silica gel chromatography (20% Hexane/EtOAc to 30% Hexane/EtOAc) to afford a yellow oil which was subjected to a second silica gel chromatography (DMC) to provide the aldehyde intermediate 4-(2-Trifluoromethyl-benzoimidazol-1-yl)- benzaldehyde as a white solid (4.0 g).

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

Reference:
Patent; SYNTA PHARMACEUTICAL CORP.; WO2006/34402; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference 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: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

The synthetic route of 10364-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 15965-31-8, name is 5-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. Quality Control of 5-Chloro-1H-imidazole

2.2. Synthesis of 1-[(4-chloro-lH-imidazol-1-yl) methyl]-4-(3, 4, 5-trifluorophenyl)- pyrrolidin-2-one 72 using thionyl chloride. Alternatively to method 2.1, 1-imidazol-1-ylmethyl-pyrrolidin-2-ones derivatives can also be obtained by a similar reaction of the hydroxymethyl derivative with successively thionyl choride in toluene for 16 h at room temperature followed by quenching of the chloromethyl derivative with an imidazole in the presence of Et3N at room temperature. For example, 1-hydroxymethyl-4- (3, 4,5-trifluoro-phenyl)- pyrrolidin-2-one reacts with thionyl chloride and 4-chloroimidazole to afford 1- [ (4- chloro-lH-imidazol-1-yl) methyl]-4- (3, 4,5-trifluorophenyl)-pyrrolidin-2-one 72 LC/MS (MH+): 330/332.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15965-31-8, its application will become more common.

Reference:
Patent; UCB, S.A.; WO2005/54188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem