Month: July 2021

Synthetic Route of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 3-tert-butyl-5-bromomethyl-2-hydroxybenzaldehyde [46,47] in toluene (5.0 mL) was addeddropwise to a solution of N-alkylimidazole (10.0 mmol) in toluene(20.0 mL) over 10 min at room temperature. The mixture was thenheated to reflux for 5 h. After cooling to room temperature, the pre-cipitate product was filtered, washed with toluene (3 × 5 mL) anddried under reduced pressure.

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

Reference:
Article; Duan, Shuhui; Jing, Xinyao; Li, Dandan; Jing, Huanwang; Journal of Molecular Catalysis A: Chemical; vol. 411; (2016); p. 34 – 39;,
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. 1072-62-4, name is 2-Ethyl-1H-imidazole, A new synthetic method of this compound is introduced below., COA of Formula: C5H8N2

2-Ethyl imidazole (1.01 g, 10.5 mmol) dissolvedin acetonitrile (25 mL) was combined with potassium hydroxide (0.58 g, 10.3mmol) and stirred for 30 minutes at 80C. 2-(Bromomethyl)naphthalene (1.73 g, 7.8 mmol) was added and the mixture wasstirred and heated at 80C overnight. The reaction mixture was filtered toremove a white solid (presumed to be potassium bromide) and the volatiles wereremoved from the filtrate to yield a yellow oil. The oil was suspended withdichloromethane (40 mL) and washed with a basic aqueous solution (1 x 30 mL)and water (3 x 30 mL). The organic layers were dried with magnesium sulfate andconcentrated to a yellow oil. The oil was resuspended in acetonitrile (7 mL)and 2-(chloromethyl)quinoline (1.59 g, 9.0 mmol) was added to the solution. Themixture was stirred and heated at 80C overnight. A white solid precipitatedfrom the hot acetonitrile and was filtered, washed with acetonitrile, and driedin air to yield 4-Cl (0.850 yield). MP = 204-207C. HRMS (ESI+) calcd for C26H24N3+[M-Cl] of m/z = 378.1965, found m/z = 378.2000. 1H NMR (500 MHz,DMSO- d6) delta = 8.48 (1H, d,Ar, J = 8.8 Hz), 8.03 (2H, t, Ar, J = 8.3 Hz), 7.98 (1H, m, Ar), 7.93 (3H, m,Ar), 7.90 (1H, m, Ar), 7.76 (2H, m, Ar), 7.64 (2H, m, Ar), 7.58 (2H, m, Ar),7.50 (1H, m, Ar), 5.90 (2H, s, CH2), 5.76 (2H, s, CH2),3.17 (2H, q, CH2, J = 7.6 Hz) 0.93 (3H, t, CH3, J = 7.6Hz). 13C NMR (125 MHz, DMSO- d6)delta = 154.2 (Ar), 149.1 (Ar), 146.7 (Ar), 137.4 (Ar), 132.7 (Ar), 132.5 (Ar),132.5 (Ar), 130.1 (Ar), 128.7 (Ar), 128.3 (Ar), 128.0 (Ar), 127.7 (Ar), 127.7(Ar), 127.2 (Ar), 126.9 (Ar), 126.7 (Ar), 126.6 (Ar), 126.4 (Ar), 125.0 (Ar),123.1 (Ar), 122.2 (Ar), 119.9 (Ar), 52.2 (CH2), 50.8 (CH2),16.6 (CH2), 11.2 (CH3). Crystal data for 4-Cl?H2O: C26H26N3O1Cl1,M = 431.95, Monoclinic, a =34.6333(13) A, b = 9.5796(4) A, c = 13.6475(5) A, beta = 92.286(2), V = 4524.8(3) A3, T = 100(2) K, space group C2/c, Z= 8, 16910 reflections measured, 4589 [R(int) = 0.0411]. The final R1 values were 0.0475 (I > 2sigma(I)). The final wR(F2)values were 0.1118 (I > 2sigma(I)).The final R1 values were0.0650 (all data). The final wR(F2) values were 0.1215 (alldata).

The synthetic route of 1072-62-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; DeBord, Michael A.; Wagers, Patrick O.; Crabtree, Steven R.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 2; (2017); p. 196 – 202;,
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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 144689-93-0

Example 6:; (5-MethyI-2-oxo-l,3-dioxol-4-yI)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2- (2H-tetrazoI-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate (olmesartan medoxomil) (Ie); Step I: 5-(2-Hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(N-(2-trimethylsilylethoxymethyl) tetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-ethylcarboxylate (Vd); 2-Propyl-5-[(l-hydroxy-l-methyl)ethyl]-3H-imidazole-4-ethylcarboxylate (0.808 g, 0.0033675 mol) was added to the two isomers (IVb) (1.5 g, 0.0033675 mol) and K2CO3 (0.558 g, 0.0040382 mol) in anhydrous DMF (10 mL) under N2 atmosphere. The mixture was stirred at room temperature for 17 hrs (TLC monitoring: cyclohexane/AcOEt 6:4). The mixture was partitioned between water and AcOEt. The organic layer was washed with water (3 times), dried over Na2SO4 and concentrated under reduced pressure to give a residue (1.8 g) that was purified by flash chromatography on silica (cyclohexane/AcOEt 6:4) to give the isomer (Vd1) (0.499 g) and the isomer (Vd2) (0.206 g) as oils. Yield: 35%. (Vd1) (isomer with lower elution time):1H-NMR (400 MHz, CDCl3, delta): -0.03 (s, 9H, Me3Si), 0.92 (t, J=8.2Hz, 2H, SiCH2CH2O), 0.96 (t, J=7.2Hz, 3H, CH2CH2CH3), 1.18 (t, J=7.2etaz, 3H, OCH2CHi), 1.64 (s, 6eta, CMe2), 1.67-1.76 (m, 2H5 CH2CH2CH3), 2.66 (t, J=7.6Hz, 2H, CH2CH2CH3), 3.66 (t, J=8.2Hz, 2H, SiCH2CH2O), 4.22 (q, J=7.2etaz, 2H, OCH2CH3), 5.44 (s, 2H, ArCH2N), 5.78 (s, 2H, OCH2N), 6.84-6.86 (m, 2H) 7.14-7.16 (m, 2H) 7.41-7.43 (m, IH) 7.46-7.56 (m, 2H) 7.84- 7.86 (m, IH) (aromatic protons).(Vd2) (isomer with higher elution time): 1H-NMR (400 MHz, CDCl3, delta): -0.10 (s, 9H, Me3Si), 0.70 (t, J=8.4Hz, 2H, SiCH2CH2O), 0.92 (t, J=7.4Hz, 3H, CH2CH2CH5), 1.13 (t, J=7.0etaz, .3eta, OCH2CH3), 1.60 (s, 6eta, CMe2), 1.62-1.71 (m, 2H, CH2CH2CH3), 2.58 (t, J=7.8Hz, 2H, CH2CH2CH3), 3.39 (t, J=8.4Hz, 2H, SiCH2CH2O), 4.17 (q, J=7.2etaz, 2H, OCH2CH3), 5.05 (s, 2H, ArCH2N), 5.38 (s, 2H, OCH2N), 6.81-6.83 (m, 2H) 7.05-7.07 (m, 2H) 7.49-7.52 (m, 2H) 7.55-7.57 (m, IH) 7.61- 7.65 (m, IH) (aromatic protons).

According to the analysis of related databases, 144689-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; S.I.M.S. S.r.l. – SOCIETA ITALIANA MEDICINALI SCANDICCI; WO2008/12852; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2403-66-9, 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. 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Methyl Iodide (839muL, 13.48 mmol) was added to a mixture of the 3-(lH-benzimidazol- 2-yl)propan-l-ol (2.5g, 14.19 mmol) and Et3N (2.16mL, 15.6 mmol) in DCM (100 mL) at O0C. The reaction stirred for 40 minutes, was warmed to room temperature and stirred 1 hour. DMF (50 mL) was added and continued stirring for 1 hour. Cesium carbonate (4.62g, 14.19 mmol) and methyl iodide (839muL, 13.48 mmol) were added and the reaction stirred overnight. The reaction was diluted with EtOAc, washed with water, saturated sodium bicarbonate and brine. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude solids were triturated with ethyl ether/hexane (1 :2) to give the title compound (1-21: step 1) as a solid. Data for 1-21: step 1: ESI+ MS: 191.1[MH]+.

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, 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2006/127550; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]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. SDS of cas: 152628-02-9

General procedure: To a solution of 1,7′-dimethyl-2′-propyl-1H,3’H-2,5′-bibenzo[d]imidazole 3 (2 mmol) and tetrabutylammonium bromide (0.2 mmol) in benzene (25 mL), a solution of 50% NaOH (25 mL) was added at 0 C followed by the addition of sulfonyl chloride 4 (2.2 mmol). The reaction mixture was stirred vigorously at room temperature for 5-6 h and the reaction was monitored by TLC. After the completion of the reaction, aqueous phase was separated and the organic phase was washed with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulphate and concentrated to give crude products which were purified by column chromatography over silica gel using hexane-EtOAc (6:4) mixture as eluent.

The synthetic route of 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roopashree, Rangaswamy; Mohan, Chakrabhavi Dhananjaya; Swaroop, Toreshettahally Ramesh; Jagadish, Swamy; Raghava, Byregowda; Balaji, Kyathegowdanadoddi Srinivas; Jayarama, Shankar; Basappa; Rangappa, Kanchugarakoppal Subbegowda; Bioorganic and Medicinal Chemistry Letters; vol. 25; 12; (2015); p. 2589 – 2593;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 16042-25-4, name is 2-Imidazolecarboxylic acid, molecular formula is C4H4N2O2, 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 C4H4N2O2

Example 130 (3.2 mg, 5.4 imol), 1H-imidazole-2-carboxylic acid (9.1 mg, 0.082 mmol) and DIEA (4.8 pi, 0.027 mmol) were dissolved in DMF (0.5 mL). HATU (2.07 mg, 5.44 imol) was added, and the reaction mixture was allowed to stir at rt for 2 h.The reaction mixture was concentrated, and the residue was purified by RP HPLC to provide the product (2.2 mg, 58%) as a clear glass (bis TFA salt). MS(ESI) m/z 455.3 (M+H)t ?HNMR(SOOMHz, CD3CN) oe 7.92(s, 1H), 7.87 (s, 1H), 7.57 (s, 2H), 7.17 (m, 3H), 6.80 (t, J=0.96 Hz, 1H), 5.45 (s, 2H), 4.65-4.92 (m, 2H), 4.29 (s, 2H), 3.65-3.99 (m,2H), 2.96 (t, J=5.91 Hz, 2H). Analytical HPLC: RT = 3.34 mm (Method A).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16042-25-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 614-97-1, 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 614-97-1 as follows.

a 4-Iodo-5-methyl-1H-benzoimidazole A solution of 5-methyl-1H-benzoimidazole (132 mg, 1.0 mmol) and NIS (248 mg, 1.10 mmol) in 1 mL of TFA was reflux for 1 hr and then cooled to RT. Treated with 30 mL of EtOAc, the mixture was neutralized with sat. NaHCO3 solution. The organic layer was washed with H2O (10 mL), brine (10 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5% MeOH/CH2Cl2) gave 78 (30%) of product as a white solid: 1H-NMR (CDCl3; 400 MHz) delta 8.07 (d, 1H), 7.57 (br s, 1H), 7.22 (d, 1H, J=8.4 Hz), 2.59 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C8H7IN2, 259.0 (M+H), found 259.2.

According to the analysis of related databases, 614-97-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5, name: 1H-Benzo[d]imidazole-2-carbaldehyde

Example 5 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone (Indo 5) 0.15 g (0.5 mmol) 5-(2-methylphenylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.12 g pale yellow solid, with a yield of 55.8percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.82 (s, 1H), 11.70 (s, 1H), 9.44 (s, 1H), 8.20 (s, 1H), 8.00 (s, 1H), 7.82 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=8.0 Hz), 7.61 (dd, 1H, J=16.8 Hz), 7.38 (t, 1H), 7.30 (t, 1H), 7.00-7.15 (m, 5H), 2.09 (s, 3H). ESI-MS m/z: 429 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is 2-methylphenylaminosulfo, and R2 is hydrogen.

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-Benzo[d]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); 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. Product Details of 75370-65-9

Preparation of 1-(4-(dimethylamino)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea 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 1a (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.; EP2377850; (2011); 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. 1243204-92-3, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1243204-92-3

Example B3 a) Preparation of compound 4 A mixture of intermediate 1 (443 mg, 2.08 mmol), 4-fluorobenzoic acid hydrazide (320 mg, 2.08 mmol) and K2CO3 (143 mg, 1.04 mmol) in n-BuOH (15 ml) was heated in the microwave at 120 0C for 12 h. The solvent was removed under reduced pressure and the resulting residue partitioned between EtOAc/H2O. The phases were separated. The aq. phase was extracted with EtOAc, and the combined organic extracts were washed with brine and dried (MgSO^. Filtration and concentration under reduced pressure gave the crude product which was purified by column chromatography over silica gel (eluent: 100:0 to 90: 10 DCM/MeOH, gradient elution). The product fractions were collected and evaporated to yield 450 mg of compound 4 (62.0 %).

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 1243204-92-3.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; WU, Tongfei; GIJSEN, Henricus, Jacobus, Maria; ROMBOUTS, Frederik, Jan, Rita; BISCHOFF, Francois, Paul; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; DE CLEYN, Michel, Anna, Jozef; PIETERS, Serge, Maria, Aloysius; MINNE, Garrett, Berlond; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; SURKYN, Michel; WO2011/6903; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem