Tag: M.W=100-200

Application of 670-96-2,Some common heterocyclic compound, 670-96-2, name is 2-Phenyl-1H-imidazole, molecular formula is C9H8N2, 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.

Placing 2-phenylimidazole in an amount of 8.6 g (60 mmol) into a flask having a dropping funnel, and after replacing the atmosphere with argon gas, 180 milliliter of tetrahydrofuran was added. Under cooling with ice, n-butyllithium of 1.56 mol/liter in an amount of 39.1 milliliter (61 mmol) was dripped down into the solution spending 30 minutes and subsequently, 8.6 g(61 mmol) of methyl iodide dissolved into 10 milliliter of tetrahydrofuran was dripped down. After termination of dripping down, the resultant solution was reacted at the room temperature for 3 hours. Concentrating the reacted solution and extracting the resultant solid using 150 milliliter of methylene chloride, it was washed three times using 150 milliliter of water. After drying an organic layer with the use of magnesium sulfate, the solvent was removed. Refining the crystals by means of silicagel column (hexane / methylene chloride), 6.1 g of 1-methyl-2-phenylimidazo Intermediate6-1b as white crystals was obtained (yield: 69 %). The white crystals were confirmed as the aimed compound from 1H-NMR spectrum. The measurement result is shown as follows: 1H-NMR(CDCl3): delta 7.29-7.67 (m,5H), delta 6.93-7.10 (m,2H), delta 3.69 (s,3H)

The synthetic route of 670-96-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1647554; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Synthesis of 1-(1-methyl-1H-imidazol-2-yl)piperazine 1.0 g (6.2 mmol) 2-bromine-1-methyl-1H-imidazol was fused with 3.2 ml (37.0 mmol) piperazine at 145 C. and stirred for 18 h at this temperature. After cooling to RT, the residue was received in 10% aq. hydrochloric acid and washed with AE. Alkalic adjustment was subsequently performed with a 10% aq. NaOH sol. (pH>12) and extraction with DCM. The organic phase was dried over MgSO4, filtered and concentrated in a vacuum. In this process, 780 mg (4.7 mmol, 76%) 1-(1-methyl-1H-imidazol-2-yl)piperazine was obtained.

The synthetic route of 2-Bromo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2008/261996; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, 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 106429-57-6, COA of Formula: C9H8N2O3

A suspension of benzimidazolone 2 (25.0 g, 0.130 mol, 1 eq) in POCl3 (150 mL) was heated to reflux for 7 h. The excess of POCl3 was evaporated and the residue was neutralized with saturated NaHCO3 solution. The precipitate was collected by filtration and dried in vacuo. The aqueous phase was extracted with DCM, dried over MgSO4 and the solvent was removed under reduced pressure. The light brown solids obtained this way were of high purity and could be used in the next step without further purification (19.7 g, 93.6 mmol, 72 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Zellmann, Felix; Thomas, Laura; Scheffer, Ute; Hartmann, Roland K.; Goebel, Michael W.; Molecules; vol. 24; 4; (2019);,
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. 50995-95-4, name is 2-Propylimidazole, A new synthetic method of this compound is introduced below., COA of Formula: C6H10N2

Copper (I) Iodide (0.038g) and D-histidine (0.062g) in DMSO (15ml) was stirred under an atmosphere of argon at 11O0C for 30 minutes when 3-(4-bromophenyl)-1 ,4- diazaspiro[4.5]dec-3-en-2-one (D6) (0.614g), 2-propylimidazole (264mg) and potassium carbonate (0.553g) was added and heating was continued at 11 O0C for 5 days when the mixture was poured into a mixture of sodium bicarbonate solution and ethyl acetate. The mixture was stirred for 2 hours, filtered and the filtrate was separated. The ethyl acetate layer was dried over sodium sulphate, evaporated and the residue was chromatographed on a silica column eluted with 0-5% 2M methanolic ammonia/DCM to give the title compound (0.2g).1H NMR (CDCI3) delta: 1.4 (3H, t), 1.5 – 1.85 (obs, m), 1.9 – 2.1 (4H, m) 2.7 (2H, t), 7.00 (1 H, m), 7.09 (1 H, m), 7.4 (2H, m), 7.82 (1 H, br), 8.55 (2H, m). Mass Spectrum (LC/MS): Found 337 (MH+). Ret. time 1.87 min.

The synthetic route of 50995-95-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/34061; (2009); A1;,
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

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

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

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

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

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