Tag: M.W=100-200

7189-69-7, 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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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 solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
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.

To the solution of 1H-benzimidazol-5-amine 121 (0.68 g, 5.11 mmol) in acetic acid (20 mL), the Compound 120a (1.06 g, 5.62 mmol) was added and stirred at room temperature for 20 minutes. TMSCN (1 mL) was added dropwise to the reaction mixture and continuously stirred for 2 hours. After reaction completing, the reaction mixture was concentrated under reduced pressure to yield a viscous liquid. The viscous liquid was diluted with ethyl acetate (10 mL) and water. The diluted solution was adjusted to the pH 6-7 with ammonia at an ice-bath. The neutralized solution was extracted with ethyl acetate (20 mL x 4), dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a viscous dark-yellow solid. The solid was dissolved in ethyl acetate (15 mL) and brine (15 mL). The mixture was stirred at room temperature for 2 minutes to form the pale-yellow precipitates. The pale-yellow precipitates was filtered and washed with water. The filtrate was dried over sodium sulfate and concentrated under reduced pressure to obtain the pale- yellow solid. Those pale-yellow solids were combined as the desired product 122a at a yield of 96%.

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:
Patent; SHIH, Chuan; NATIONAL HEALTH RESEARCH INSTITUTES; ACADEMIA SINICA; CHEN, Chih-Hao; CHEN, Chiung-Tong; WANG, Hwei-Jiung; HUANG, Kai-Fa; (130 pag.)WO2020/47360; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

To a 200 mL eggplant-shaped flask equipped with a magnetic stirrer, 18.7 g (100 mmol) of 2-trifluoromethylbenzimidazole, 16.6 g (120 mmol) of potassium carbonate, 17.0 g (120 mmol) of methyl iodide and 100 mL of acetone were added. The mixture was heated to reflux for 3 hours. After the reaction mixture was cooled, water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain 19.7 g of gray crystals. Yield: 98%. 1H-NMR (400 MHz, CDCl3, relative to TMS) delta (ppm): 3.96 (s, 3H), 7.37-7.46 (m, 3H), 7.88 (d, J=6.0 Hz, 1H).

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

Reference:
Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; KUMIAI CHEMICAL INDUSTRY CO., LTD.; KAWAZOE, Kentaro; YOSHIOKA, Kotaro; (107 pag.)US2017/197920; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

614-97-1, A common compound: 614-97-1, name is 5-Methyl-1H-benzo[d]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.

General procedure: In a typical reaction procedure, benzimidazole (1mmol), different derivatives of ammonia (1mmol), 0.5 mol% [Ru(bpy)3]Cl2 were taken in a single necked round bottom flask. The reaction mixture was stirred at room temperature under blue light. The completion of the reaction (indicated by disappearance of the starting material and formation of new product, observed by TLC (30:70%) ethyl acetate and hexane. After the product formation 15 ml ethyl acetate and 10 ml water were added. The organic reactants and product were taken out with ethyl acetate and [Ru(bpy)3]Cl2 were dissolved and taken out with water.

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-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Siddiqui; Ibad, Farah; Ibad, Afshan; Abdul Waseem, Malik; Watal, Geeta; Tetrahedron Letters; vol. 57; 1; (2016); p. 5 – 10;,
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

4-Iodo-1H-imidazole (Compound 25, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)Triethylamine (2.1 mL, 15 mmol) and trityl chloride (3.4 g, 12 mmol) were added and the mixture was stirred at room temperature (25 C.) for 17 hours under an argon gas atmosphere. After completion of the reaction, water was added and the mixture was extracted twice with dichloromethane. The combined dichloromethane layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent: chloroform / n-hexane = 1/1 ? chloroform) to obtain compound 26 (4.1 g, 9.3 mmol, yield 93%).

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; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; OKUMURA, YUKI; IZAWA, AKIHIRO; AKAMA, KEI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (28 pag.)JP2015/93831; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

1615-14-1, Name is 2-(1H-Imidazol-1-yl)ethanol, 1615-14-1, 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.

General procedure: The following examples were prepared using general procedure described below: A solution of corresponding alcohol (3 equiv) in THF (3 mE) was stirred in an ice-water bath under an atmosphere of Argon. Potassium tert-butoxide (1.0 M, 3 equiv) was added in a single portion and the mixture was stirred at 00 C. for 30 minutes, and then 2-fluoro-5-(4- ((4-(4-(oxetan-3-yl)piperazin-1 -yl)phenyl)amino)-1 ,3,5-tri- azin-2-yl)benzonitrile was added (1 equiv). The mixture was stirred for 2 hr at it Afier the mixture cooled to room temperature, water was added, and mixture evaporated under reduced pressure. Solids were purified via preparative HPEC (5-65% acetonitrile in water, 0.1% trifluoroacetic acid buffer)to yield the final product.

Statistics shows that 2-(1H-Imidazol-1-yl)ethanol is playing an increasingly important role. we look forward to future research findings about 1615-14-1.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

16042-25-4, 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.

To a solution of 1H-imidazole-2-carboxylic acid (0.179) in N,N-dimethylformamide (DMF) (3 mL) was added alanine tert-butyl ester hydrochloride (0.22 g), diisopropylethyl amine (0.27 mL) and HOBT (0.41 g) before cooling to 0 C. and the reaction mixture was then treated with EDC HCl (0.32 g). The cooling bath was removed and the reaction mixture was stirred at ambient temperature for 18 hrs before being diluted with ethyl acetate and washed with water and brine, dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to afford the sub-title compound as a colourless oil (0.263 g, 73%): 1H NMR 400 MHz CDCl3 1.50 (9H, s), 1.51 (3H, d, J 7.2), 3.70 (1H, m), 7.28 (2H, s), 7.78 (1H, d, J 7.6), 11.49 (1H, br s).

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

Reference:
Patent; Randle, John C.R.; US2005/267101; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common compound: 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, 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. 1615-14-1

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.72 g (9.8 mmol) of 1-tetradecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.70 g (73%). Mp= 40-42 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz (CDCl3), delta, ppm, J/Hz: 0.87 t (3H, J=6.8), 1.25-1.33m (22 H),1.87-1.91m (2 H), 3.98 t (2H, J=4.9), 4.26 t (2H, J=7.5), 4.53 t (2H,J=4.9), 7.31 s (1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 309.5 [MBr]+.Calculated, %: C19H37 N2 OBr: C 58.60; H 9.57; N 7.19; Br 20.52;found, %: C 58.02; H 10.05; N 7.21; Br 19.99.

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, 1615-14-1, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
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. 7189-69-7 name is 1,1′-Sulfonyldiimidazole, 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. 7189-69-7

To a solution of compound Int-TG1-3 (530 mg, 1.2 mmol) in dry THF (25 ml) was added 1,1 ?-Sulfonyldiimidazole (477 mg, 2.4 mmol) and C52CO3 (196mg, 0.6 mmol). After 18hours under reflux, the mixture was quenched with 2 N aq. HC1 (100 mL). The organic layer was extracted with EtOAc (2 x 20 mL), dried over anhydrous Mg504, filtered and concentrated. The residue was purified by column chromatography to produce the compound Int-TG12 (396 mg, 58%).?H-NIVIR (400 MHz, CDC13) 5 7.84 (s, 1H), 7.35 (s, 1H), 7.34-7.3 1 (m, 1H), 7.20-7.16(m, 2H), 7.05 (t, 1H), 6.86 (m, 1H), 5.51-5.45 (m, 2H), 5.10 (dd, J = 3.6 Hz, 1H), 4.98 (d, J = 8Hz, 1H), 2.24 (s, 3H), 2.13(s, 3H), 2.07 (s, 3H), 2.04 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1′-Sulfonyldiimidazole, and friends who are interested can also refer to it.

Reference:
Patent; INTOCELL, INC.; PARK, Taekyo; WOO, Sung Ho; KIM, Sunyoung; PARK, Suho; CHO, Jongun; JUNG, Doohwan; SEO, Donghoon; LEE, Jaeho; LEE, Sangkwang; YUN, Sanghyeon; LEE, Hyang Sook; PARK, Okku; SEO, Beomseok; (316 pag.)WO2019/8441; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 4857-06-1, name is 2-Chloro-1H-benzo[d]imidazole, molecular formula is C7H5ClN2, 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. 4857-06-1

2-Chloro-5-nitrobenzimidazole (19) To 210 mL of fuming HNO3, 2-chlorobenzimidazole (13.42 g, 87.95 mmole) was added portionwise over a period of 10 min with stirring and ice-H2 O cooling. After the addition, the cooling bath was removed and stirring was continued at room temperature overnight. This reaction mixture was cooled to ~0 C., poured into 300 mL of ice, and neutralized carefully with conc. NH4 OH to ~pH 8. The resulting suspension was filtered. The yellowish solid product was washed with portions of H2 O and air-dried. The filtrate and washings were combined and extracted with EtOAc (200 mL*2). The EtOAc solution was washed with sat. NaCl solution (200 mL*2), dried (Na2 SO4), and evaporated to give 1.3 g of a yellowish solid. The solid was combined with the major part of the product and was recrystallized from MeOH to give 16.34 g (5 crops, 94%) of 19 as yellowish crystals. mp 235-237

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4857-06-1, its application will become more common.

Reference:
Patent; The Regents of the University of Michigan; US5360795; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem