Tag: M.W=100-200

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. 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol

EXAMPLE 7 A lithium diisopropylamine solution (prepared from 65 ml of a 2.2 molar solution of butyl lithium in hexane and 14.5 g of diisopropylamine in 150 ml of tetrahydrofuran) was added dropwise at a temperature of -60 C. within 15 minutes to a solution of 22 g of 1-methyl-2-nitroimidazole-5-methanol in 300 ml of tetrahydrofuran and 150 ml of dimethylformamide. The mixture was stirred at -60 C. for 30 minutes and treated with 28 g of p-toluenesulphonyl chloride in 150 ml of tetrahydrofuran. After removing the cooling, warming to room temperature and adding 300 ml of ice/water, the mixture was extracted three times with 300 ml of ethyl acetate each time. The combined extracts were washed with 150 ml of saturated sodium chloride solution and evaporated under reduced pressure. The residue was purified on 800 g of silica gel with ethyl acetate/dichloromethane (1:3, v/v). After a forerun of 1.5 l, the next 1.5 l were collected and evaporated. Recrystallization from 70 ml of toluene yielded 12 g (50%) of 5-(chloromethyl)-1-methyl-2-nitroimidazole, m.p. 100-101 C.

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 39070-14-9.

Reference:
Patent; Hoffmann-La Roche Inc.; US4515790; (1985); A;,
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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, A new synthetic method of this compound is introduced below., SDS of cas: 60-56-0

2-Mercapto-l-methylimidazole (84 mg, 0.73 mmol) was added neat to a solution of 2- bromo-l-[l-(4-chloro-phenyl)-cyclopropyl]-ethanone (200.5 mg, 0.73 mmol) in CH3CN (5 mL) at room temperature, then Et3N (0.203 mL, 1.46 mmol) was added neat to the mixture and the reaction was stirred over night. The reaction was then quenched by addition of a small spatula of resin 2-chlorotrityl chloride, stirred for IH then the mixture was filtered and concentrated under vacuum. The crude mixture was purified by flash chromatography (hexane/EtOAc gradient 0-50%) to afford the title compound (216.5 mg, 97%) as cream-yellow solid. TLC single spot at R/ 0.13 (hexane/EtOAc 7:3); Mp = [95.5- 97.0 0C]; 1H NMR (270 MHz, CDCl3): delta 1.19 (q, J = 3.7 Hz, 2H), 1.63 (q, J = 3.2 Hz, 2H), 3.62 (s, 3H), 3.86 (s, 2H), 6.87 (d, J = 1.2 Hz, IH), 6.98 (d, J = 1.2 Hz, IH), 7.32 (d, J = 0.7 Hz, 4H); LC/MS (APCI) m/z 307 (M++H); HPLC tr = 1.88 min (100%) in 10% water-acetonitrile.

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; STERIX LIMITED; WO2009/106817; (2009); A2;,
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. 137049-00-4, name is 1-Methyl-1H-imidazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5ClN2O2S

General procedure: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. The title compound was prepared by reaction of (5-(3-aminophenyl)thiophene-2-yl)(2,6-difluoro-3-hydroxyphenyl)methanone (30)(100 mg, 0.30 mmol) and 1-methyl-1H-imidazole-4-sulfonyl chloride (81 mg, 0.45mmol) according to Method C. The product was purified by CC (dichloromethane/methanol95:5); yield: 72% (103 mg). 1H NMR (500 MHz, acetone-d6)delta 9.17 (s, 1H), 9.01 (s, 1H), 7.75-7.72 (m, 2H), 7.64-7.61 (m, 2H), 7.54 (d, J= 4.1 Hz, 1H), 7.50-7.43 (m, 1H),7.39-7.34 (m, 2H), 7.21 (td, J= 9.4, 5.5 Hz, 1H), 7.04 (td, J= 8.8, 1.9Hz, 1H), 3.76 (s, 3H);13C NMR (125 MHz, acetone-d6) delta 180.7, 155.1, 153.6,151.6, 149.5, 147.5, 143.3, 142.7, 140.7, 140.1, 138.3, 134.5, 130.9, 126.2,122.5, 121.9, 120.4, 118.4, 112.6, 112.4, 34.2; MS (ESI): 476.21 (M+H)+)+; HPLC purity ? 98% (Rt = 12.54 min).

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; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
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. 46006-36-4, name is 1H-Benzimidazole-7-carboxylic acid belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 46006-36-4

Example 144 : N-(5-((5-(4-(dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyridin-3- yl)-1H-benzo[d]imidazole-4-carboxamide. [0711] To a mixture of 4-(6-((5-aminopyridin-3-yl)amino)pyridin-3-yl)-N,N- dimethylbenzamide (80 mg, 0.24 mmol) in pyridine (2 mL) was added lH-benzo[d]imidazole-4-carboxybc acid (58 mg, 0.36 mmol) and EDOHC1 (92 mg, 0.48 mmol), the reaction mixture was stirred at 50 C for 2 h to give a brown suspension. LCMS (Rt = 0.660 min; MS Calc’d: 477.2; MS Found: 478.1 [M+H]+). The mixture was concentrated under reduced pressure to give a residue. The residue was purified by washing with MeOH (5 mL) to give a crude product. Then further purified by prep-HPLC (0.225% FA as an additive) to give N-(5-((5-(4- (dimethylcarbamoyl)phenyl)pyridin-2-yl)amino)pyridin-3-yl)-1H-benzo[d]imidazole-4- carboxamide (7.9 mg, yield: 7%) as a white solid. LCMS (Agilent LCMS 1200-6140 A, mobile phase: from 99% [water + 0.1% FA] and 1% [MeCN + 0.1% FA] to 95% [water + 0.1% FA] and 5% [MeCN + 0.1% FA] in 0.6 min, then changed to 100% [MeCN + 0.1% FA] under this condition for 3.4 min, finally back to 99% [water + 0.1% FA] and 1 % [MeCN + 0.1% FA] and under this condition for 0.5 min.) purity is 97.48%, Rt = 2.126 min; MS Calc’d: 477.2; MS Found: 478.3 [M+H]+. NMR (400 MHz, DMSO-rie) d 2.91-3.05 (6H, m), 7.04 (1H, d, J = 8.8 Hz), 7.45-7.53 (3H, m), 7.76 (2H, d, J = 8.4 Hz), 7.85-7.94 (1H, m), 8.00-8.07 (2H, m), 8.61-8.72 (3H, m), 8.74-8.80 (1H, m), 8.83-8.92 (1H, m), 9.75 (1H, br s).

The synthetic route of 46006-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETRA PHARMA CORPORATION; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; KESICKI, Edward A.; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (450 pag.)WO2019/126731; (2019); 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. 939-70-8, name is 1-(1H-Benzo[d]imidazol-2-yl)ethanone, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-(1H-Benzo[d]imidazol-2-yl)ethanone

General procedure: To a solution of 2-acetylbenzimidazole 3 (0.800 g, 5.00 mmol) in ethanol (50 mL) were added 60% aqueous potassium hydroxide (15 mL) and 4-fluorobenzaldehyde (0.620 g, 5 mmol) at 0 C with stirring. The reaction mixture was stirred at room temperature until complete consumption of starting material (monitored by TLC, petroleum ether/chloroform, 1/3, V/V). The crushed ice and diluted hydrochloric acid solution were added for total precipitation of the yellow solid (0.846 g), which were obtained by vacuum filtration and then recrystallized in ethanol.

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; Liu, Han-Bo; Gao, Wei-Wei; Tangadanchu, Vijai Kumar Reddy; Zhou, Cheng-He; Geng, Rong-Xia; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 66 – 84;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

35203-44-2, A common compound: 35203-44-2, name is 1-Propyl-1H-imidazole, 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.

Weigh 184g of 1,3-propane sultone, and add 1L of ethyl acetate to the reactor, and install a constant pressure dropping funnel.Magnetic stirrer and reflux condenser, slowly add 123g N-propyl imidazole when heated to 60 ° C in a water bath.After the completion of the dropwise addition, the system was kept at 80 ° C for 2 h to produce a white precipitate;The system was subjected to vacuum filtration, and the cake was washed with ethyl acetate.It is dried in an oven at 100 ° C, and the obtained product is 1-(3-sulfonate)propyl-3-propylimidazolium salt;The 1-(3-sulfonate)propyl-3-propylimidazolium salt is dissolved in water, and concentrated sulfuric acid is added to carry out the reaction at 85 ° C.The water is then removed to give a pale yellow viscous liquid product which is the 1-propyl-3-propanesulfonic acid imidazolium hydrogensulfate ionic liquid.

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, 1-Propyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou Geng Lan Biological Technology Co., Ltd.; Dong Qiuyue; Yang Caihua; (6 pag.)CN109053372; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The chemical industry reduces the impact on the environment during synthesis 16042-25-4, name is 2-Imidazolecarboxylic acid, I believe this compound will play a more active role in future production and life. 16042-25-4

5 (1.00 g, 3.30 mmol) and 1H-imidazole-2-carboxylic acid(0.40 g, 3.60 mmol) were dissolved in 3 mL sulfolane, and 12 mLPOCl3 was added. The reaction mixturewas stirred at 85 C for 18 h,then cooled to room temperature, poured into 200 mL ice water.NaOH was added to adjust the PH to 7. The mixturewas filtered anddried in vacuo to give 92 mg of 11-3 as gray solid: 7% yield. 1H NMR(300 MHz, DMSO-d6) delta 13.83 (s, 1H), 8.77 (d, J = 5.4 Hz, 1H), 8.01 (d,J = 9.0 Hz, 1H), 7.52 (s, 1H), 7.36 (d, J = 2.5 Hz, 1H), 7.28 (d, J =5.2 Hz,2H), 7.18 (dd, J= 9.2, 2.6 Hz, 1H), 5.82 (s, 2H), 3.90 (s, 3H); m.p.:205-207 C; HRMS (ESI+) m/z 380.0914 (380.0924 calcd forC17H14N7O2S+, [M+H]+).

The chemical industry reduces the impact on the environment during synthesis 16042-25-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuan, Haoliang; Liu, Qiufeng; Zhang, Li; Hu, Shihe; Chen, Tiantian; Li, Huifang; Chen, Yadong; Xu, Yechun; Lu, Tao; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 491 – 502;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 32673-41-9, 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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step F Preparation of 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in dry DMF (250 ml) at ambient temperature was added Et3 N (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in of DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hrs, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the title compound as a white solid which was sufficiently pure for use in the next step.

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, 4-Imidazolemethanol hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5817678; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, 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. Recommanded Product: 1-Methyl-1H-imidazole-2(3H)-thione

Dithiafulvalenyl compound 1 (0.2 mmol), mercapto-thiazole 2 (2 mmol, 10 equiv.), and I2 (0.6 mmol, 3 equiv., 152.4 mg) were dissolved in DMSO (3 mL). The reaction mixture was stirred at 25 C for 12 h under N2 atomsphere. Then quenched with a saturated solution of Na2S2O3 and stirred for half an hour, the solution was extracted with dichloromethane (CH2Cl2). The organic layer was separated, and dried over Na2SO4. Then the organic solvent was removed in vacuo to afford the respective thiadiazole-based dithiafulvalene (DTF) derivatives (3), which were purified by column chromatography (silica gel, PE / CH2Cl2) to afford pure substances.

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

Reference:
Article; Fu, Huimin; Zhao, Bangtun; Zhu, Weimin; Tetrahedron Letters; vol. 60; 2; (2019); p. 124 – 128;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 15108-18-6, 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. 15108-18-6, name is 2-Hydrazinyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-hydrazinobenzimidazole (750 mg;5mmol) in a mixture of 10mL of water and 0.75mL of concentrated HCl was gradually added 1,1,3,3-tetramethoxypropane(820mL; 5mmol). The resulting mixture was heated at reflux for 2 h, then was allowed to cool and filtered.The filtrate was neutralised with solid potassium carbonate,causing the product to precipitate as a pale tan solid, which was filtered and dried in vacuo. Yield 650mg (71%). m.p. 233-2358C; dH(500MHz, d6-DMSO) 6.66 (m, br, 1H,H2), 7.19-7.21 (m, 2H, H6 H7), 7.46 (d, 1H, J 6.1 Hz,H5), 7.58 (d, 1H, J 7.7 Hz, H8), 7.94 (d, 1H, J 1.5 Hz,H3), 8.59 (d, 1H, J 2.9 Hz, H1), 13.10 (s, br, 1H, H4);dC(125MHz, d6-DMSO) 109.2, 111.6, 118.4, 122.2, 122.5,129.1, 133.7, 141.7, 142.9, 146.1; m/z (HR-ES-MS)185.0821 ([M H], calculated for C10H9N4 185.0822);y max(KBr)/cm21 2943m br, 1628m, 1574s, 1479m, 1460s,1387m, 1324m, 1273m, 1226m, 1076s, 927s, 740s.

The synthetic route of 2-Hydrazinyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hawes, Chris S.; Kruger, Paul E.; Supramolecular Chemistry; vol. 27; 11-12; (2015); p. 757 – 771;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem