Month: February 2021

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. 112809-54-8, name is 4-((1H-Imidazol-1-yl)methyl)benzonitrile, A new synthetic method of this compound is introduced below., category: imidazoles-derivatives

(a) A suspension of potassium tert-butoxide (61.6 g) in dimethylformamide (500 mL) is stirred and cooled to -10 (ice-salt bath), and a solution of 4-(1-imidazolylmethyl)-benzonitrile (45.6 g) in dimethylformamide (250 mL) is added so that the reaction temperature remains below 0. The resulting solution is stirred at 0 for 0.5 hour and then a solution of 4-fluorobenzonitrile (38.3 g) in dimethylformamide (100 mL) is added while keeping reaction temperature below 5. After 0.75 hour, the reaction mixture is neutralized to pH 7 by addition of sufficient 3N hydrochloric acid and the bulk of the solvents are then removed under reduced pressure. The residue is diluted with water (500 mL) and the crude product is extracted into ethyl acetate (3*200 mL). The combined extracts are then extracted with 3N hydrochloric acid (3*150 mL) and, after washing the latter acid extracts with ethyl acetate (100 mL), the solution is made basic (pH 8) with 6N ammonium hydroxide and the product is again extracted into ethyl acetate (3*150 mL). The combined extracts are dried (MgSO4), decolorized by treatment with charcoal, and then evaporated to give crude 4-[alpha-(4-cyanophenyl)-1-imidazolylmethyl]-benzonitrile as an oil.

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; Ciba-Geigy Corporation; US4749713; (1988); A;; ; Patent; Ciba-Geigy Corporation; US4978672; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, 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 52099-72-6, Application In Synthesis of 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

1-isopropenylbenzimidazolone 1.74 g (0.01 mol)And 0.72 g (0.01 mol) of acrylic acid were placed in a 100 mL reaction flask,30 mL of dried methylene chloride was added,Stir to complete dissolution, add 0.2 mL of triethylamine.And then weighed three phosgene 1.19g (0.004moL) dissolved in dry 10mL dichloromethane,Ice bath slowly drop in the reaction bottle.After the dropwise addition, the reaction system was returned to room temperature,Continue to stir 5 ~ 8h, after the end of the reaction,To the reaction system was added 20 mL of a saturated aqueous solution of sodium hydrogencarbonate,Full shock after the static phase separation, the organic phase washed with water, magnesium chloride drying,Degassed under reduced pressure and purified by silica gel column chromatography (eluent petroleum ether / ethyl acetate = 4/1)To give 2.11 g of the title compound (yield 92.5%),

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

Reference:
Patent; Institute of Pesticide Science,Northwest A & F University(NWAFU); Ji, Zhiqin; Wu, Wenjun; Wei, Shaopeng; (9 pag.)CN102816121; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 870837-48-2, 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. 870837-48-2, name is 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: NaOAc anhydrous (17.6mg, 0.21mmol), the appropriate aldehyde derivative (0.14mmol), and intermediate 6 (25.4mg, 0.07mmol) were dissolved in AcOH (3mL) and stirred at 110C for 16h. After cooling, the mixture was neutralized to pH 8 by addition of NH4OH and extracted with DCM. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, DCM/MeOH 15/1 v/v including 1% of NH4OH) to produce the final target compounds.

The synthetic route of 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkamhawy, Ahmed; youn Kim, Nam; Hassan, Ahmed H.E.; Park, Jung-eun; Yang, Jeong-Eun; Elsherbeny, Mohamed H.; Paik, Sora; Oh, Kwang-Seok; Lee, Byung Ho; Lee, Mi Young; Shin, Kye Jung; Pae, Ae Nim; Lee, Kyung-Tae; Roh, Eun Joo; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 39861-21-7, These common heterocyclic compound, 39861-21-7, name is 4-(5-Chloro-1H-benzo[d]imidazol-2-yl)aniline, 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.

(c) N-[4-(5-Chloro-1H-benzoimidazol-2-yl)-phenyl]-2-cyclohexylmethyl-succinamic acid methyl Ester This compound was prepared by the procedure described in Example 1 part (a) from 4-(5-Chloro-1H-benzoimidazol-2-yl)-phenylamine and (R)-2-(Cyclohexylmethyl) succinic acid 1-methyl ester to give the crude product (2.0 g, 51%), which was used in the next step without further purification.

The synthetic route of 39861-21-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bekkali, Younes; Betageri, Rajashehar; Emmanuel, Michel Jose; Hickey, Eugene Richard; Liu, Weimin; Patel, Usha R.; Spero, Denice Mary; Thomson, David S.; Ward, Yancey David; Young, Erick Richard Roush; US2001/41700; (2001); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 112809-54-8, 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. 112809-54-8, name is 4-((1H-Imidazol-1-yl)methyl)benzonitrile belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(a) A solution of n-butyl lithium (25 mL of 2.1M reagent in hexane, 0.0525 mole) is added dropwise in an N2 atmosphere to a solution of di-isopropylamine (5.6 g) in tetrahydrofuran (100 mL) which is maintained at -20. This cold solution is then added dropwise to a solution of 4-(1-imidazolylmethyl)benzonitrile (9.15 g) in tetrahydrofuran (250 mL) which is maintained at -50 during addition and for 30 minutes subsequently. The reaction mixture is then cooled to -70 and methyl iodide (10.7 g) is added, all at once. The reaction is stirred at -70 for 30 minutes and then without external cooling for 10 hours. The reaction is quenched by addition of water (300 mL) and extracted with diethyl ether (3*100 mL). The combined ether extracts are extracted with 3N hydrochloric acid (3*60 mL) and the acid extracts are made basic (pH 9) with 6N sodium hydroxide. The crude product is extracted into ether (3*60 mL), and after drying (MgSO4) and solvent evaporation, 4-[1-(1-imidazolyl)ethyl]benzonitrile is obtained. The crude material is dissolved in acetone and treated with ethereal HCl to afford the hydrochloride salt, m.p. 184-186.

The synthetic route of 4-((1H-Imidazol-1-yl)methyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4978672; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 6160-65-2, These common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, 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.

A flask was charged with (8S,10R,llS,12S,13R,14S)-12-hydroxy-ll-(4- methoxyphenyl)- 10,13 -dimethy 1-2, 6,7, 8,9, 11,12,14,15,16-decahy dro- 1 H- cyclopenta[a]phenanthrene-3,17-dione (Step H) (270 mg, 0.66mmol) and azeotroped with toluene. DCM (7 mL) was added, followed by triethylamine (0.28mL, 1.98mmol, 3 eq), and di(imidazol-l-yl)methanethione (1.18 g, 6.61mmol, 10 eq). The reaction was stirred under argon at rt for one day, then another portion of di(imidazol-l-yl)methanethione (1.1 g) was added. After another day, another 700 mg of di(imidazol-l-yl)methanethione was added. The reaction was stirred for 2 more days. Then the reaction was quenched with diluted HCl (chromatography to give the title compound (265 mg, 77%). m/z (ESI, +ve ion) 541.3 (M+Na)+.

Statistics shows that 1,1′-Thiocarbonyldiimidazole is playing an increasingly important role. we look forward to future research findings about 6160-65-2.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; SUN, Daqing; MCGEE, Lawrence R.; DU, Xiaohui; ZHU, Liusheng; YAN, Xuelei; REW, Yosup; EKSTEROWICZ, John; MEDINA, Julio C.; ZHOU, Haiying; BALBAS, Minna Delarae; FANTIN, Valeria R.; (98 pag.)WO2017/112909; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, molecular formula is C4H3N3, 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. Recommanded Product: 1H-Imidazole-4-carbonitrile

a) 1-(2-Trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile A flask charged with imidazole-4-carbonitrile (0.50 g, 5.2 mmol) (Synthesis, 677, 2003), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (0.95 mL, 5.3 mmol), K2CO3 (1.40 g, 10.4 mmol), and acetone (5 mL) was stirred for 10 h at RT. The mixture was diluted with ethyl acetate (EtOAc) (20 mL) and washed with water (20 mL) and brine (20 mL) and the organic layer dried over MgSO4. The crude product was eluted from a 20-g SPE cartridge (silica) with 30percent EtOAc/hexane to give 0.80 g (70percent) of the title compound as a colorless oil: Mass spectrum (CI (CH4), m/z) Calcd. for C10H17N3OSi, 224.1 (M+H), found 224.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57090-88-7, its application will become more common.

Reference:
Patent; Illig, Carl R.; Ballentine, Shelley K.; Chen, Jinsheng; DesJarlais, Renee Louise; Meegalla, Sanath K.; Wall, Mark; Wilson, Kenneth; US2007/249593; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3287-79-4, 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. 3287-79-4, name is 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5,6-dimethyl-2-mercaptobenzimidazole (9.45 g, 0.053 mole), 1,8-diazabicyclo [5.4.0] undec-7-ene (9.7 g, 0.064 mole) and 1-iodo-2,2,2-trifluroethane (13.4 g, 0 064 mole) in 210 ml dimethylformamide is heated (50 C. for 41/2 hours), poured onto ice and water (1500 ml), and the precipated solid collected by filtration and dried. The product is recrystallized from toluene-ligroine giving 5,6-dimethyl-2-(2,2,2-trifluoroethyl-mercapto)-1H-benzimidazole (3.4 g, 0.013 mole), m.p. 150-163 C.

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, 5,6-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US4608381; (1986); 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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Iodo-1-trityl-1H-imidazole

Cul (21.8 mg, 0.12 mmol), /nmv-N,N’-dimcthylcyclohcxanc- 1 ,2-diaminc (36.1 iiL, 0.23 mmol) and K2CO3 (317 mg, 2.29 mmol) were added to a solution of 1-169 (500 mg, 1.15 mmol) in toluene (6.25 mL) in a sealed tube while N2 was bubbling. After 10 min, 4-chloro-lH-pyrrolo[3,2-c]pyridine [60290-21-3] (227 mg, 1.15 mmol) was added. The reaction mixture was stirred at room temperature for 10 min, and at 100 C for 20 h. The reaction mixture was cooled to room temperature and diluted with NaHCCh (sat., aq.) and extracted with EtOAc. The organic layer was dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude mixture was purified by flash column chromatography (silica, heptane/EtOAc, gradient from 100:0 to 80:20) to afford 1-170 (430 mg, 81%).

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; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33468-69-8, 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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-6-cyclohexyl-pyrane-2-one (257mg, L. OOMMOL) and 4-trifluoromethyl- 1H-imidazole (204mg, 1. 50MMOL) were dissolved in acetonitrile (50ML) in a 100mL flask, and K2CO3 (414mg, 3. 00MMOL) and KI (25mg, 10% w/w) were added thereto. The reaction solution was heated under reflux. After 15 hours, the reaction solution was cooled down to room temperature and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel using MC: MEOH (20: 1) as eluent. The fractions containing the product were combined and evaporated to give a white solid (298mg, 96%). ‘H-NMR (CDC13) ; 8 = 7.99 (s, 1H), 7.64 (s, 1H), 6.17 (dd, 2H), 2.53 (m, 1H), 2.1- 1.2 (m, LOH).

The chemical industry reduces the impact on the environment during synthesis 4-(Trifluoromethyl)-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; C & C RESEARCH LABORATORIES; WO2004/50624; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem