Month: November 2020

288-32-4, Name is 1H-Imidazole, 288-32-4, 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.

In a 50 mL round-bottomed flask, imidazole (1 mmol), phenylboronicacid (1.2 mmol), K2CO3 (1.5 mmol), nanocatalyst (15mol% with respect to imidazole substrate) were added andstirred in MeOH-H2O (1:1) under air at r.t. for the requiredtime, monitoring by TLC. After completion, the mixture wasdiluted with H2O and the product was extracted with EtOAc(3¡Á). The combined extracts were washed with brine (3¡Á) anddried over Na2SO4. The product was purified using columnchromatography (60-120 mesh silica gel, eluting with EtOAc-hexane). The product was isolated as white solid. 1H NMR (400MHz, CDCl3): delta = 7.87 (s, 1 H), 7.50-7.47 (m, 2 H), 7.40-7.35 (m,3 H), 2.28 (m, 1 H), 7.21 (s, 1 H) ppm. 13C NMR (100 MHz,CDCl3): delta = 137.4, 135.6, 130.3, 129.9, 127.6, 121.6, 118.3 ppm.

Statistics shows that 1H-Imidazole is playing an increasingly important role. we look forward to future research findings about 288-32-4.

Reference:
Article; Borah, Raju Kumar; Raul, Prasanta Kumar; Mahanta, Abhijit; Shchukarev, Andrey; Mikkola, Jyri-Pekka; Thakur, Ashim Jyoti; Synlett; vol. 28; 10; (2017); p. 1177 – 1182;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39021-62-0, 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 39021-62-0 as follows.

A mixture of (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 1-methyl-1H-imidazole-5-carbaldehyde (220 mg, 2 mmol) in ethyl propionate (20 mL) was cooled to 0 C. Then a solution of sodium ethoxide in ethanol [sodium (184 mg, 8 mmol) in ethanol (10 mL)] was added dropwise. After the addition, the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL¡Á4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 to 3:7) to give ethyl 3-(1-methyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (170 mg, yield 23%). LC-MS (ESI) m/z: 376 (M+1)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 39021-62-0, and friends who are interested can also refer to it.

Reference:
Patent; LEAD THERAPEUTICS, INC.; US2010/35883; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

10364-94-0, Name is (1H-Imidazol-1-yl)(phenyl)methanone, 10364-94-0, 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.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) and 0.15 mL DMF (dry) was added DBU(0.2 equiv.), and the mixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in 0.5 mL MeCN (dry) was added to the reaction mixture in two portions and it was allowed to stir at 50C for 8 h. MeCN was removed under reduced pressure and the resulting mixture was purified by flashcolumn chromatography (ethyl acetate/petroleum ether = 1:1 to 10:1) to afford benzoylated products.

Statistics shows that (1H-Imidazol-1-yl)(phenyl)methanone is playing an increasingly important role. we look forward to future research findings about 10364-94-0.

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

3097-21-0, 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. 3097-21-0 name is 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, 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.

Take 1,3-dimethyl-1,3-dihydro-2H-benzo [d] imidazol-2-one (1.0 g, 6.1 mmol),Add to chlorosulfonic acid and react at room temperature for 5 hours;After the reaction is completed, water is added to precipitate a solid, which is filtered with suction, recrystallized, and filtered with suction, and the filter cake is dried under infrared.A gray solid was obtained with a yield of 88%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; Mo Jun; Li Qihang; Yang Hongyu; Chen Yao; Chen Tingkai; Li Qi; Guo Yan; Liu Zongliang; Feng Feng; Liu Wenyuan; (19 pag.)CN110776494; (2020); A;,
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

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

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

152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, 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. 152628-02-9

In a 2 litre reaction flask 500 ml of methyl isobutyl ketone was added followed by 100 gm of 2-n-propyl-4-methyl-6-( -methylbenzimidazol-2′-yl)benzimidazole. The reaction mass was stirred and a solution of 40 gm sodium hydroxide in 300 ml water was added. To this solution, 10 gm tetra butyl ammonium hydrogen sulphate and 80 gm of 4-chloromethyl-2′- cyanobiphenyl was added. The reaction mass was warmed to 80 C and maintained for 4 hours at 80 to 85 C. The completion of the reaction was monitored by TLC using mobile phase chloroform : methanol (9:1). After completion of the reaction, the mass was cooled to 20 C, maintained 3 hours at 15 to 20 C. The product which precipitated out was filtered, washed with methyl isobutyl ketone, followed by water to yield 126 gm of 2-cyano-4′-(2″-n-propyl-4″-methyl- 6″-(r”-methylbenzimidazol-2″‘-yl)benzimidazol-l”- ylmethyl) biphenyl, melting at 196 – 198 C. C 80.53%, H 5.70%, N 14.20%; m/z = 496.64 1H NMR DMSO d6 400 Mhz : 5ppm 0.96 – 0.99 (t, 3H) 1.75 – 1.84 (m, 2H) 2.62 (s, 3H) 2.89 – 2.93 (t, 2H) 3.80 (s, 3H) 5.67 (s, 2H) 7.18 – 7.92 (m, 14H)

Statistics shows that 152628-02-9 is playing an increasingly important role. we look forward to future research findings about 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5’-bibenzo[d]imidazole.

Reference:
Patent; U AMARNATH, Amarnath; U SURYAKIRAN, Suryakiran; WO2014/27280; (2014); 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

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