Month: February 2021

Electric Literature of 2302-25-2, The chemical industry reduces the impact on the environment during synthesis 2302-25-2, name is 4-Bromo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-bromo-1H-imidazole (2.59 g, 17.6 mmol, Eq: 1.00) and di-tert-butyl dicarbonate (4.04 g, 4.3 ml, 18.5 mmol, Eq: 1.05) were combined with tetrahydrofuran (19 ml). Dimethylaminopyridine(43.1 mg, 352 imol, Eq: 0.02) was added and the reaction was stuffed at 25C for 1.5 h. Thecrude reaction mixture was concentrated in vacuo. The residue was taken up in ethyl acetate and washed with a solution 1M of hydrogen chloride, water, saturated sodium bicarbonate and brine. The organic layer was dried and concentrated in vacuo to afford the desired compound as an off- white solid (4.2 g, 95%).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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: 1H,1’H-2,2′-Biimidazole

Example 14: Synthesis of (tetrakis(1-phenylpyrazolato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(ppz)2BIm]2) [0300] [0301] Under argon atmosphere, into a 100 mL Schlenk flask equipped with a stirrer were placed 308 mg (0.30 mmol) of di-mu-chloro-tetrakis(1-phenylpyrazolato) diiridium(III), 40 mg (0.30 mmol) of 2,2′-biimidazole and 60 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 7 hours. Subsequently, 83 mg (0.63 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 16 hours. After the completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, and then methylene chloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure. The resultant crude reaction product was subjected to column chromatography with alumina (developing solvent: methylene chloride : 0.5 % triethylamine) for purification, to provide 180 mg of the desired compound as a pale ocher solid. (Isolation yield: 55 %) Additionally, tetrakis(1-phenylpyrazolato)(mu-biimidazolyl) diiridium(III) was a novel compound, which had the following properties: [0302] 1H-NMR (400MHz, CD2Cl2, delta (ppm)); 8.35 (dd, 4H), 7.29 (dd, 4H), 6.76-6.80 (m, 8H), 6.61-6.56 (m, 4H), 6.50-6.48 (m, 4H), 6.39-6.39 (dd, 4H), 6.18 (s, 4H) FD-MS (M/Z): 1088 M+

The synthetic route of 492-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 73746-45-9, These common heterocyclic compound, 73746-45-9, name is 5-Iodo-2-methyl-1H-imidazole, 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.

Step C: Triethylamine (13.4 mL, 96.2 mmol) followed by trityl chloride (20.1 g, 72.1 mmol) were added to an ambient temperature solution of 4-iodo-2-methyl-1H-imidazole (ca. 10 g, 48.1 mmol) in methylene chloride (90 mL). After stirring at ambient temperature for 2 days, the reaction mixture was diluted with methylene chloride and washed with water and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-15% acetone/methylene chloride afforded the title compound.

The synthetic route of 73746-45-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, David; Franklin, Christopher L.; Guzzo, Peter R.; Lin, Linus S.; Lo, Michael M.C.; Nargund, Ravi P.; Sebhat, Iyassu K.; US2010/22598; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, 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. category: imidazoles-derivatives

2,4-Dichloro-phenol (190 mg, 1.17 mmol) is dissolved in methylene chloride (2 mL). To the solution is added (3-methyl-2-nitro-3H-imidazol-4-yl)-methanol (115 mg, 0.732 mmol) and triphenylphosphine (211 mg, 0.805 mmol). The mixture is stirred at room temperature until a solution is achieved. The solution is then cooled in an ice bath and treated with diisopropyl azodicarboxylate, DIAD (158 xL, 0.805 mmol). After 1 hour the ice bath is removed and the mixture is stirred overnight at room temperature. Crude product is purified on a silica gel column to isolate the product mixed with triphenylphosphine oxide. The solids are triturated with t-butyl methyl ether to remove the triphenylphosphine oxide to afford 5-(2,4-dichloro- phenoxymethyl)-l-methyl-2-nitro-lH-imidazole. MS (ESI+) for C11H9Cl2N3O3m/z 301.1 (M+H)+.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENCIA CORPORATION; KHAN, Shaharyar; (80 pag.)WO2018/129258; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-50-2, 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. 3034-50-2, name is Imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 1-Trityl-1H-imidazole-4-carbaldehyde STR49 To dimethylformamide (100 mL) was added imidazole-4-carboxaldehyde (10 g, 0.104 mol, Aldrich Chemical Corp.) and triethylamine (20.5 mL, 0.147 mol). A solution of trityl chloride (40 g, 0.143 mol) in dimethylformamide (300 mL) was added, followed by stirring at 25 C. for 6 hours. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (1.5 L) and 1N citric acid (350 mL). The phases were separated, and the organic phase was washed with brine, dried over anhydrous magnesium sulfate, and filtered. Concentration of the solution in vacuo gave a white solid, 27.59 g, 78% yield. NMR was consistent with structure. MS: APCI: M-1: 337.2 (M: 338.41).

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

Reference:
Patent; Warner-Lambert Company; US6143766; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, This compound has unique chemical properties. The synthetic route is as follows.

3-Hydroxy-4-aminobenzonitrile (2.68 g, 20 mmol) was dissolved in 15 mL anhydrous THF.C bis(1H-imidazolyl)methylimine (3.54 g, 22 mmol) was added and the mixture was refluxed for 16 hr.Extracted with ethyl acetate, the crude product was recrystallizedIntermediate D 2-Amino-6-cyanobenzoxazole (2.8 g, yield 88%).

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

Reference:
Patent; Zhejiang Haizheng Pharmaceutical Co., Ltd.; Wang Yaping; Zheng Guojun; Liu Lifei; Shi Lei; Zhou Jiebo; Ding Fang; (16 pag.)CN109251187; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 616-47-7, These common heterocyclic compound, 616-47-7, name is 1-Methyl-1H-imidazole, 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 literature procedure for the synthesis of the title compound was adopted. 2 A solution of N-methyl-1H-imidazole (280 muL, 290 mg, 3.50 mmol) in anhydrous THF (7 mL) was cooled to -78C and n-BuLi (2.5 M in hexanes, 2.2 mL, 3.60 mmol) was added dropwise by syringe under stirring. The resulting yellow solution was stirred for 30 minutes at -78C where upon chlorotrimethylsilane (465 muL, 399 mg, 3.67 mmol) was added dropwise by syringe; after the addition the resulting reaction mixture was allowed to return to room temperature and the stirring was continued for 1 h. The reaction was then cooled back to -78C, ethylchloroformiate (350 muL, 398 mg, 3.67 mmol) was added and the resulting mixture was allowed to warm up to room temperature and further stirred for 1h. The reaction was quenched with water (1 mL) and the solvents were evaporated under reduced pressure. The obtained crude product was dissolved in dichloromethane (100 mL), washed with water (3 x25 mL) and brine (1 x 25 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with EtOAc as eluent, the chromatographic fractions containing the required compound were collected and concentrated under reduced pressure, affording the title compound 1f as a colorless liquid(152 mg, 37%).

Statistics shows that 1-Methyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 616-47-7.

Reference:
Article; Bellina, Fabio; Lessi, Marco; Marianetti, Giulia; Panattoni, Alessandro; Tetrahedron Letters; vol. 56; 25; (2015); p. 3855 – 3857;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3705-87-1, 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. 3705-87-1, name is 2-Chloro-1-isopropyl-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows.

4.7. 2-[4-(1H-imidazol-4-yl)piperidin-1-yl]-1-(1-methylethyl)-1H-benzimidazole. 47.3 ml (0.25 mole) of sodium methylate are added to a solution of 27.6 g (0.123 mole) of the above compound. The mixture is stirred for 15 minutes and it is, concentrated under vacuum to two thirds its volume, and 200 ml of dichloromethane are added. The sodium chloride precipitate which forms Is filtered. The filtrate is concentrated under vacuum. The crystallized residue is reacted with 12 g (0.061 mole) of 2-chloro-1-(1-methylethyl)-1H-benzimidazole in 60 ml of 3-riethybutan-1-ol at 120 C. for 36 hours. The precipitate of excess (8 g) piperidine monohydrochloride is filtered. The filtrate is evaporated to dryness. The residue obtained is purified on a silica gel column eluding with a mixture of dichloromethane and methanol in proportions ranging from 95:5 to 90:10 v/v. The pure fractions are combined and evaporated. The solid is washed with ether and dried under vacuum. 14.3 g of compound are obtained. Melting point: 183 C.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1-isopropyl-1H-benzo[d]imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Synthelabo; US5280030; (1994); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 10364-94-0, The chemical industry reduces the impact on the environment during synthesis 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

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, (1H-Imidazol-1-yl)(phenyl)methanone, other downstream synthetic routes, hurry up and to see.

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

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 934-22-5 as follows. Recommanded Product: 6-Aminobenzimidazole

To a stirred solution of 5-amino-benzimidazole (290mg, 2. 2MMOL) in anhydrous DMF (lOmL) under N2 was added caesium carbonate (980mg) The resulting mixture was stirred at 70C for 60 min. To this was added a solution of 6-CHLORO-N-[(15)-1-PHENYLETHYL] PYRAZIN-2-AMINE (470mg) in DMF (5mL) and the resulting mixture was then heated at reflux for 48h. The DMF was removed under reduced pressure and the residue diluted with chloroform. The organic layer was washed with aqueous NA2CO3, dried (NA2SO4) and the solvent removed under reduced pressure to furnish the crude product. Column chromatography using dichloromethane-methanol (95: 5 No. 92: 8) as eluant separated two fractions from unreacted starting material. The higher Rf fraction was assigned as the 6-isomer (276mg, 42%). 1H-n. m. r. (CDCl3) 81. 64 (d, 3H, J= 6.9Hz, CH3), 2.90 (br s, 2H, NH2), 5.05 (m, 1H, CH), 5.21 (d, 1H, NH), 6.70 (dd, 1H, /= 8.7, 2. 1Hz, benzimid-H), 6.97 (d, 1H, J = 1. 8Hz, benzimid-H), 7.28-7. 43 (m, 5H, Ph-H), 7.58 (d, 1H, J= 8.4Hz, benzimid-H), 7.84 (s, 1H, pyraz-H), 8.08 (s, 1H, pyraz-H), 8.21 (s, 1H, benzimid-H). m/z (ES) 331 (M++H). The lower fraction was assigned as the 5-isomer (170mg, 26%),’H-n. m. r. (CDCl3) 81. 64 (d, 3H, J= 6. 9HZ, CH3), 2.85 (BR S, 2H, NHZ), 5.01 (m, 1H, CH), 5.19 (d, 1H, NH), 6.70 (dd, 1H, J= 8.7, 2. 1Hz, benzimid-H), 7.11 (d, 1H, J= 1. 8Hz, benzimid-H), 7.29-7. 40 (m, 5H, Ph-H), 7.51 (d, 1H, YE8. 7Hz, benzimid-H), 7.81 (s, 1H, pyraz-H), 8.10 (s, 1H, pyraz-H), 8.32 (s, 1H, benzimid-H). m/z (ES) 331 (M++H).

According to the analysis of related databases, 934-22-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYTOPIA PTY LTD; WO2003/99811; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem