Tag: M.W=100-200

Related Products of 405173-97-9, The chemical industry reduces the impact on the environment during synthesis 405173-97-9, name is 2-(2-Chloroethyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 73 norfloxacin (1.920g, 0.006mol), 97 potassium carbonate (0.830g, 0.006mol) and 98 potassium iodide (0.100g, 0.006mol) in 99 acetonitrile (100mL) was stirred at 50C for 1h. After the mixture was cooled to room temperature, compound 8a (1.000g, 0.006mol) was added. The reaction mixture was then heated at 50C for 3h. After the reaction was completed (monitored by TLC, chloroform/methanol (50/1, V/V)), the reaction was cooled to room temperature and treated with 90 formic acid to adjust the pH value to 5.5-6.5. After the acetonitrile was removed under reduced pressure, the mixture was purified by flash silica gel column eluting with chloroform/methanol (60/1, V/V) to give the pure target 100 compound 13a as white power (1.120g). Yield: 41.7%.

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, 2-(2-Chloroethyl)-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Ling; Addla, Dinesh; Ponmani, Jeyakkumar; Wang, Ao; Xie, Dan; Wang, Ya-Nan; Zhang, Shao-Lin; Geng, Rong-Xia; Cai, Gui-Xin; Zhou, Cheng-He; Li, Shuo; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 160 – 182;,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1615-14-1

Example 3; Preparation of Hydroxyethylimidazole Acrylate by Transesterification with Various Catalysts; At a temperature of 60 C., methyl acrylate (MA) and hydroxyethylimidazole (HEI) in a molar ratio of 5:1 were heated in the presence of 50 ppm of phenothiazine, 500 ppm of hydroquinone monomethyl ether and 1.25 mol % of a catalyst (based on hydroxyethylimidazole) for 5 h.After the end of the reaction time, the mixture was analyzed by gas chromatography. The results are compiled in table 2.; It can be seen that, in all cases, the transesterification did not lead to full conversion, since the methanol formed was not removed under the experimental conditions.Consequently, the by-product, according to GC-MS analyses, was the 1,4 addition product of methanol to hydroxyethylimidazole acrylate: Only when Zr(acac)4 was used was a very small amount of by-product formed, since this catalyst virtually completely suppresses this side reaction.It was found that various catalysts such as K3PO4, K2CO3, NaOH, K(acac), Zr(acac)4 and DBU are very suitable for the transesterification of methyl acrylate with hydroxyethylimidazole.

According to the analysis of related databases, 1615-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; US2010/4462; (2010); 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 1848-84-6 as follows. Safety of 2-Ethyl-1H-benzo[d]imidazole

A mixture of 4-(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-3- isopropylpiperazin-2-one (198 mg, 0.49 mmol), 2-ethylbenzimidazole (78 mg, 0.53 mmol), Pd2(dba)3 (11.1 mg, 2.5 molpercent), Xphos (23.1 mg, 10 molpercent) and Cs2CO3 (237 mg, 0.16 mmol) in dioxane (4 mL) was purged with argon gas then heated at 110 0C, for 17 h, in a sealed tube. The reaction mixture was loaded onto an Isolute.(R). SCX-2 cartridge, washed with MeOH then the desired product eluted with 2 M NH3/MeOH in DCM. The resulting residue was purified by column chromatography (Si-PCC, 0-10percent MeOH in EtOAc) to give 648 (196 mg, 78percent) as a white solid. LCMS: (Method I): Rx 3.37 min, [M+H]+ 518.2 1H NMR (400 MHz, CDCl3d): delta 8.05-8.00 (m, 1 H), 7.79-7.75 (m, 1 H), 7.30-7.23 (m, 2 H), 6.02 (s, 1 H), 4.50-3.96 (m, 4 H), 4.09 (d, J = 13.6 Hz, 1 H), 3.94 (d, J = 13.6 Hz, 1 H), 3.89 (s, 3 H), 3.87 (t, J = 4.80 Hz, 4 H), 3.63-3.54 (m, 1 H), 3.37 (q, J = 7.5 Hz, 2 H), 3.34-3.28 (m, 1 H), 3.13-3.04 (m, 1 H), 3.03 (d, J = 5.5 Hz, 1 H), 2.74-2.66 (m, 1 H), 2.25-2.14 (m, 1 H), 1.46 (t, J =7.5 Hz, 3 H), 1.11 (d, J = 6.8 Hz, 3 H), 1.03 (d, J = 6.8 Hz, 3 H)

According to the analysis of related databases, 1848-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CASTANEDO, Georgette; CHAN, Bryan; GOLDSTEIN, David Michael; KONDRU, Rama K.; LUCAS, Matthew C.; PALMER, Wylie Solang; PRICE, Stephen; SAFINA, Brian; SAVY, Pascal Pierre Alexandre; SEWARD, Eileen Mary; SUTHERLIN, Daniel P.; SWEENEY, Zachary Kevin; WO2010/138589; (2010); 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. 106429-57-6, name is Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O3

Potassium tert-butoxide (2.57 g) was added to a solution of 2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester (2 g) in DMA (30 ml). Allyl bromide (2 ml) was added, and the mixture was stirred for 2 h at room temperature. The mixture was acidified with 2N aqueous HCl and then extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (2.2 g) as a yellow oil. MS (m/e)=273.2 [M+H+].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 106429-57-6.

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249124; (2010); 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, A new synthetic method of this compound is introduced below., Product Details of 104619-51-4

Example 24: [4-(5-AmJnO- Pl, 3,41 oxadiazot-2-yl)-pyridin-3-yl1-(2-chloro-4-iodo- phenvh-amine; To a solution of 3-(2-Chloro-4-iodo-phenylamino)-isonicotinic acid hydrazide (150mg, 0.39mmol, 1 eq), in DMSO (2mL) C- (Di-imidazol-i-yl)-methyleneamine (124mg, 0.77mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight and then poured into water. The product was isolated by filtration (135 mg). LC/MS (Method A) [5.22min; 414(M+1 )]

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; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); 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. 52099-72-6, name is 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(Prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one

To a solution of 1-isopropenylbenzimidazolone (500 mg, 2.8 mmol) in dry THF (40 mL) are added triphenylphosphine (902 mg, 3.4 mmol) and (4-Methyl-benzo[>]thiophen-3-yl)-methanol (563 mg, 3.2 mmol). Then diisopropyl azodicarboxylate (0.70 mL, 3.4 mmol) is added drop wise into the above solution after it is cooled down to 0 0C. The mixture is then stirred at room temperature for 5 hr and then the solvent is removed under vacuum and the residue is purified by flash column chromatography using gradient EtOAc/Hexane from 0% to 20% to give 630mg (66%) of 1 -isopropenyl-3-(4-methyl-benzo[£]thiophen-3-ylmethyl)- 1 ,3-dihydro-benzimidazol- 2-one.

The synthetic route of 52099-72-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/147697; (2008); 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 33468-69-8 as follows. Product Details of 33468-69-8

Preparation of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)-imidazol-1-yl]imidazo[4,5-c]pyridine (I-74) Under argon, 99 mg (0.27 mmol) of 6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimidazo[4,5-c]pyridine, 23 mul (0.15 mmol) of trans-N,N’-dimethylcyclohexane-1,2-diamine, 6.8 mg (36 mumol) of copper(I) iodide, 30 mg (0.22 mmol) of 4-(trifluoromethyl)-1H-imidazole and 64 mg (0.46 mmol) of potassium carbonate are added to 1 ml of degassed toluene. The vessel is closed and the reaction mixture is heated in a CEM Discover microwave reactor to 110 C. for 4 h. After cooling to room temperature, ethyl acetate is added and the mixture is filtered through a Celite bed, which is subsequently rinsed with ethyl acetate. The solvent is removed under reduced pressure and the residue is separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane). In this way, 22 mg (100% purity, 18% yield) of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)imidazol-1-yl]imidazo[4,5-c]pyridine are obtained. (log P (neutral): 3.36; MH+: 473; 1H NMR (600 MHz, CD3CN) delta ppm: 8.905 (3.0); 8.903 (3.0); 8.852 (1.6); 8.850 (1.6); 8.500 (1.9); 8.313 (1.5); 8.311 (2.1); 8.309 (1.4); 8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961 (3.4); 4.001 (16.0); 3.940 (0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5); 3.087 (1.2); 2.639 (0.7); 2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998 (195.7); 1.989 (2.7); 1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973 (26.5); 1.969 (18.0); 1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404 (0.7); 1.373 (0.6); 1.330 (4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2); 1.301 (3.4); 0.914 (0.6).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; ALIG, Bernd; ILG, Kerstin; MALSAM, Olga; GOeRGENS, Ulrich; TURBERG, Andreas; LI, Jun; ZHERSH, Sergey; ARLT, Alexander; (58 pag.)US2017/73342; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. name: 4-Amino-1H-benzo[d]imidazol-2(3H)-one

4-(aminomethyl)-N,N-dimethylbenzenamine 2i (1 g, 6.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (1 g, 6.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 350 mg of a white solid. Yield = 16% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.18 (2H, d, J = 5.6 Hz), 6.58 (2H, m), 6.69 (2H, d, J = 8.8 Hz), 6.86 (2H, m), 7.14 (2H, d, J = 8.8 Hz), 8.18 (1H, s), 9.98 (1H, bs), 10.58 (1H, bs); [M+1] 326.5 (C17H19N5O2 requires 325.37).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4, 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 104619-51-4 as follows.

A solution containing the product from step 1 (8.36 g, 54.2 mmol) and 2-amino-4-nitrophenol (8.74 g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.0 g), as a yellow solid. MS (ESI) m/e (M+H+): 180. 1H NMR (DMSO) delta: 7.857.96 (m, 3H), 7.52 (d, J=8.8 Hz, 1H).

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

COMPOUND 12.1.55: N,N-DIETHYL-4-{7-[(4-METHYL-1H-IMIDAZOL-5- YL) METHYL1-6J. 8, 9-TETRAHYDROri31DIOXOLOr4, 5-F] ISOOUINOLIN-6- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (76. 4 mg, 0.69 mmol) was added to a solution of INTERMEDIATE 5.1. 15 (122.6 mg, 0.35 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (516 mg, 2.43 mmol) was added followed by N-methyl-2- pyrrolidinone (400 I1L) and the reaction mixture stirred at RT for 18 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 55 as an oil (35.6 mg, 23%). 1H NMR (500 MHz, CDC13) : 8 1.13 (br s, 3H), 1.25 (br s, 3H), 2.09 (s, 3H), 2.55 (m, 1H), 2. 78 (m, 1H), 3.09 (m, 1H), 3.28 (br s, 2H), 3.34-3. 40 (m, 2H), 3.55 (br s, 2H), 3.59 (d, J 13.5 Hz, 1H), 4. 58 (s, 1H), 5.96 (s, 1H), 6. 21 (d, J 8 Hz, 1H), 6.55 (d, J 8 Hz, 1H), 7.28-7. 32 (m, 4H), 7.36 (s, 1H) ; 13C NMR (125 MHz, CDCl3) : 8 11. 37, 13. 11, 14.42, 22.28, 39.61, 43.64, 45.72, 49.40, 67.41, 101. 30, 106.56, 117. 66,122. 17, 126.56, 129.73, 130.71, 131.73, 133.45, 136.22, 144.81, 145.28, 145.54, 171. 54; (+) LRESIMS m/z 447.20 [M+H] +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem