Month: May 2021

Reference of 65039-05-6, 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 65039-05-6 as follows.

General procedure: 1-Butyl-3-methylimidazolidine, chloride salt (5 mmol), selenium (5 mmol), potassium carbonate (10 mmol), ethanol or acetone (5 mL) and a magnetic stirring bar were placed in a 50 mL, two-necked flask. Then the reaction mixture was vigorously stirred under reflux for the given times (see Table 2). After the reaction was complete, the resultant mixture was filtered, and the solvent evaporated under reduced pressure. Further purification by column chromatography on silica gel gave the pure product. All the products were characterised by NMR and HRMS.

According to the analysis of related databases, 65039-05-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Fengshou; Chen, Yahong; Wu, Lan; Li, Peng; Lu, Shiwei; Journal of Chemical Research; vol. 38; 6; (2014); p. 375 – 377;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 25372-03-6, 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 25372-03-6 as follows.

56 g (0.33 mol) of 1-(4-cyanophenyl)imidazole are dissolved in 560 ml water-free tetrahydrofuran in a 2000 ml one-necked flask with condenser, admixed with 234.2 g (1.65 mol) of methyl iodide, stirred briefly and allowed to stand for 48 hours without further stirring. The solid contents of the flask are subsequently slurried with ethanol, filtered off with suction and washed with ethanol until the washings are virtually colorless. The residue is dried at 70° C. under reduced pressure. The yield is 81.54 g (80percent of theory).1H-NMR (400 MHz, DMSO): delta=3.97 (s, 3H); 8.00-8.04 (m, 3H); 8.22 (d, J=9.0 Hz, 2H); 8.40 (dd, J=1.8, 1.8 Hz, 1H); 9.91 (s, 1H). Elemental analysis: calculated for C11H10IN3: C, 42.4; H, 3.3; N, 13.5; I 40.0, found: C, 42.6; H, 2.9; N, 13.6; I 40.9.

According to the analysis of related databases, 25372-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2009/18330; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 149520-94-5, The chemical industry reduces the impact on the environment during synthesis 149520-94-5, name is Ethyl 2-amino-1H-imidazole-5-carboxylate, I believe this compound will play a more active role in future production and life.

a) Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[l,2-a]pyrimidine-2-carboxylateEthyl 2-amino-lH-imidazole-4-carboxylate (6.45 mmol, 1 g) and triethyl- amine (10.04 mmol, 1.016 g) were suspended in dry ACN (30 ml) and cooled to 0 C. Acryloyl chloride (9.67 mmol, 0.875 g) dissolved in dry ACN (4 ml) was added dropwise. The resulting mixture was slowly warmed to RT and subsequently heated to 50 C for 16 h. The solvent was evaporated and the residue purified by flash chromatography. 0.358 g of the title compound was obtained. lH-NMR (400 MHz, CDC13): delta 1.37 (t, 3H), 2.92 (t, 2H), 4.18 (t, 2H), 4.37 (q, 2H), 7.40 (s, IH), 8.78 (bs, IH).

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, Ethyl 2-amino-1H-imidazole-5-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); 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. 914306-50-6, name is 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole, A new synthetic method of this compound is introduced below., name: 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-imidazole

(Step 3) Into a three-head flask, there were put 2.8 g of the intermediate body C obtained in Step 2, 1.6 g of an intermediate body D, and 50 ml of ethylene glycol, and this mixture was heated and stirred for 7 hours at 150 C. under a nitrogen atmosphere. Precipitated crystals were obtained by filtration, and the crystals obtained by the filtration were washed by methanol, and thereafter, were separated and purified by silica gel chromatography, whereby 0.7 g of the DP-1 was obtained. A structure of the compound example DP-1 was confirmed by MASS spectrum and 1H-NMR. MASS spectrum (ESI): m/z=1179 [M+] 1H-NMR (CD2CI2, 400 MHz) delta: 7.71 (2H, d, J=28.3 Hz), 7.42 (1H, t, J=28.3 Hz), 7.33-7.57 (6H, m), 7.34 (4H, t, J-33.2 Hz), 6.96 (2H, 5), 6.81-6.86 (6H, m), 6.69 (2H, d, J=33.2 Hz), 6.56-6.60 (2H, m), 6.44 (1H, t, J=23.4 Hz), 6.38 (2H, d, J=17.6 Hz), 6.32 (1H, d, J=23.4 Hz), 6.16 (2H, d, J=44.9 Hz), 2.65-2.80 (3H, m, CH of iso-Pr), 2.29-2.41 (3H, m, CH of iso-Pr), 1.26 (3H, d, J=26.3 Hz, CH3 of iso-Pr), 1.21 (6H, d, J=20.5 Hz, CH3 of iso-Pr), 0.92-1.08 (m, 27H, CH3 of iso-Pr)

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; KONICA MINOLTA ADVANCED LAYERS, INC.; OTSU, Shinya; ONO, Kaori; KATOH, Eisaku; US2013/200340; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole, 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. Computed Properties of C8H6Cl2N2

To sodium hydride (300 mg) in DMF at 0 C. was added 5,6-dichloro-2-methylbenzoimidazole (500 mg) in one portion. The mixture was stirred at 0 C. for 15 minutes, followed by addition of ethyl 6-bromohexanoate (0.66 mL). The mixture was stirred at 0 C. for another 15 minutes and then at room temperature for 1 hour. The solution was concentrated to dryness under vacuum and the residue was purified by column chromatography on silica gel to give pale brown solid (0.75 g).

The synthetic route of 5,6-Dichloro-2-methylbenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTIUM, INC.; Mao, Fei; Leung, Wai-Yee; Cheung, Ching-Ying; Hoover, Hye Eun; US9097667; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 66247-84-5,Some common heterocyclic compound, 66247-84-5, name is (1H-Imidazol-4-yl)methanamine hydrochloride, molecular formula is C4H8ClN3, 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.

Example 119A N-((1H-imidazol-4-yl)methyl)-1-(4-(2,4-difluorophenoxy)-3-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)phenyl)methanamine [1125] To a suspension of 1H-imidazol-4-ylmethylamine dihydrochloride (269 mg, 1.59 mmol) in a mixture of dichloromethane (3 mL) and methanol (1 mL) was added triethylamine (0.442 mL, 3.17 mmol). After stirring the mixture for five minutes, Example 105B (125 mg, 0.317 mmol) and acetic acid (0.181 mL, 3.17 mmol) were added. The mixture was heated at 50° C. for 1 hour. The mixture was cooled in an ice bath and sodium triacetoxyborohydride (134 mg, 0.634 mmol) was added portionwise over several minutes. After 15 minutes, the ice bath was removed and the reaction mixture was stirred 2 hours while warming to ambient temperature. The reaction mixture was quenched with 1 M sodium hydroxide (2 mL) and partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-10percent 7N methanolic ammonia in methylene chloride) to provide the title compound (90.3 mg, 62percent yield).

The synthetic route of 66247-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Le; Pratt, John; Hasvold, Lisa A.; Liu, Dachun; Dai, Yujia; Fidanze, Steven D.; Holms, James H.; Mantei, Robert A.; McDaniel, Keith F.; Sheppard, George S.; McClellan, William J.; US2014/275026; (2014); 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. 1093261-46-1, name is Methyl 5-bromo-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 5-bromo-1H-imidazole-4-carboxylate

A solution of methyl 4-bromo-1 /-/-imidazole-5-carboxylate (0.708 g, 3.5 mmol) was stirred in a solution of MeOH (20 mL) and 2N NaOH (20 mL, 40 mmol) at 40 0C for 4h, then additional 2N NaOH (20 mL, 40 mmol) was added and the reaction mixture kept at 40 0C for another hour. The reaction mixture was then acidified by addition of 1 M HCI (100 mL) and extracted with EtOAc. The organic extracts were dried (Na2SO4), and the solvent was evaporated to provide crude 4-bromo-1 /-/-imidazole-5- carboxylic acid (0.156g, 24%) as a white solid which was used without further purification.4-Bromo-lambda/-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1 /-/- imidazole-5-carboxamide trifluoroacetate was prepared in a similar manner as described herein from 3-{[3-aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5- chlorobenzonitrile (0.062 g, 0.20 mmol), 4-bromo-1 /-/-imidazole-5-carboxylic acid (0.038 g, 0.20 mmol), HATU (0.091 g, 0.24 mmol), DIPEA (0.042 ml_, 0.24 mmol) and DMF (2 ml_). Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.010 g, 8%) as a white solid. 1H NMR (400 MHz, DMSOd6) delta ppm 8.38 (br. s., 1 H), 7.82 (s, 2 H), 7.44 – 7.54 (m, 3 H), 7.38 (t, 1 H), 4.51 (d, 2 H). ES-LCMS: m/z 482.9, 484.9, 486.9 (M+1 ).

According to the analysis of related databases, 1093261-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 50591-22-5, 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 50591-22-5 as follows.

To a solution of NaH (204 mg, 8.49 mmol) in DMF (5 mL) was added 1-methyl- lH-benzo[d]imidazol-5-ol (420 mg, 2.83 mmol) at 28C. After being stirred for 5 minutes, ethyl 2-bromoacetate (568 mg, 3.4 mmol) was added and the resulting mixture stirred for a further 16 h under the reaction was complete by TLC. The mixture was treated with water (50 mL) and extracted with ethyl acetate (2×20 mL). The water layer was treated with 2N HC1 until pH 3 and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the product (160 mg, 24.1%) as white solid which was used in next step without further purification. LCMS (m/z): 207.1 (M+l).

According to the analysis of related databases, 50591-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 378203-86-2,Some common heterocyclic compound, 378203-86-2, name is Ethyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, molecular formula is C7H9N3O4, 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 degassed solution of intermediate 44a (480 mg), 2-bromo-1,4-dimethoxybenzene (1.04 g), palladium acetate (54 mg), di(1-adamantyl)-n-butylphosphine (130 mg) and potassium acetate (490 mg) in N,N-dimethyl acetamide (7 mL) was stirred under an argon atmosphere at 150 C. for 2 h. The volatiles were removed under reduced pressure and the residue was dissolved in water and was extracted with CH2Cl2. The combined organic layers were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (SiO2/50 g, Cy/2-propanol) to yield the desired compound (31% yield). [0596] LC-MS (Method 1): m/z [M+H]+=336.2 (MW calc.=335.31); Rt=3.4 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2851-13-0, name is N,N-Dimethyl-1H-benzo[d]imidazol-2-amine, 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 2851-13-0, category: imidazoles-derivatives

2-Acetylpyridine (1.12 cm3, 9.9 mmol) was added consecutively by syringe, to a solution of 2-(1-methylhydrazinyl)-1Hbenzo[d]imidazole (1.62 g, 9.9 mmol) in ethanol. The mixture was stirred and heated at 60 C for 48 h. The product was isolated by evaporation of the solvent and recrystallization of the residue from a minimum volume of CH3CN by the gradual addition of diethyl ether. Yield: 83% (2.19 g). ESI-MS: m/z (%) = 266 (100) [L+H]+, 288(30) [L+Na]+. 1H NMR (300 MHz, CD3CN): 8.21 (d, J = 4.5 Hz, 1H),7.73 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 7.8 Hz, 1H), 7.06-7.23 (m, 5H),3.48 (s, 3H, CH3-N), 3.48 (s, 3H, CH3-CN) ppm. 13C NMR (CD3CN,100 MHz): 162.04, 157.09, 155.16, 148.93, 148.72, 136.81, 136.29,127.07, 124.41, 121.62, 77.31, 76.99, 76.54, 40.26, 16.38 ppm. IR (KBr): m(C-H)ar 3075m, 3058s, 3029s, m(CC) 1580m, 1564m,1517w, 1456s; m(CN) 1442s, 1400m, 1346w, 1311s, q(C-H)1198s, 1170vs, 1143m, 1085s, 990s, 952s, 885vs; c(C-H) 837s,806m, 789s, 762m, 735m, 641s, 608s, 548m, 438s, 414s cm1. Anal.Calc. for C15H15N5 (265.32): C, 67.90; H, 5.70; N, 26.4. Found: C,67.82; H, 5.77; N, 26.32%.

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

Reference:
Article; Marcinkowski, Damian; Wa??sa-Chorab, Monika; Bocian, Aleksandra; Miko?ajczyk, Joanna; Kubicki, Maciej; Hnatejko, Zbigniew; Patroniak, Violetta; Polyhedron; vol. 123; (2017); p. 243 – 251;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem