Author: Jessica.F

Application of 152628-03-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 152628-03-0 name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

7-Methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid methyl ester (7a): Sulfuric acid (12 mL, 0.22 mol) was added to 7-methyl-2-propyl-3H-benzoimidazole-5-carboxylic acid (30 g, 136 mmol) dissolved in MeOH (670 mL, 16 mol). The mixture was refluxed for 36 hours and concentrated in vacuo. The recovered material was dissolved in 500 mL EtOAc and washed with a saturated NaHCO3 solution. The organic layer was dried over MgSO4 and concentrated to provide Intermediate (7a) as a brown solid (29.1 g). MS m/z: [M+H+] calcd for C13H16N2O2, 233.1; found 233.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Theravance, Inc.; US2008/318951; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 27231-33-0, The chemical industry reduces the impact on the environment during synthesis 27231-33-0, name is 4-Methyl-1H-benzo[d]imidazole-2(3H)-thione, I believe this compound will play a more active role in future production and life.

EXAMPLE 7 2-[[(4-Methyl-1H-benzimidazol-2-yl)thio]methyl]benzenamine The title compound was prepared by the method of Example 1 using 3.52 g of 2-mercapto-4-methylbenzimidazole instead of 2-mercaptobenzimidazole and 3.52 g of 2-(chloromethyl) aniline hydrochloride instead of 2-(chloromethyl)-N,N-dimethylaniline. Recrystallization from diethyl ether gave 1.23 g of the title compound: m.p. 125-127 C. Anal. Calc’d. for C15 H15 N3 S: C, 66.89; H, 5.61; N,15.60; S, 11.90. Found: C, 66.76; H, 5.62; N, 15.41; S, 11.87.

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-Methyl-1H-benzo[d]imidazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G.D. Searle & Co.; US5945425; (1999); A;,
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. 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-6-nitro-1H-benzo[d]imidazole

Dimethylamine (2M in THF, 15 ml_) was added to a sealable tube containing 2-chloro-5- nitro-1 H-benzo[d]imidazole (1 g, Example 181 (a)). The reaction flask was sealed and heated at 80 C for 16 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford the crude title product as a black tar (800 mg). This was used directly without purification. LCMS m/z 207.16 (M+H)+.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; DUFFY, Kevin J.; GRAYBILL, Todd L.; MOORE, Michael Lee; NEIPP, Christopher E.; RALPH, Jeffrey M.; SQUIRE, Michael Damien; (304 pag.)WO2017/153952; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

51-17-2, name is 1H-Benzo[d]imidazole, 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. SDS of cas: 51-17-2

N-Methylimidazole, quinoline, benzimidazole, iodomethaneand anhydrous NiBr2 were purchased from Sigma-Aldrich (>99%)and used as received. N-Methyl-benzimidazole was synthesizedaccording to a known literature method [10]: Benzimidazole (25.0 g, 211.6 mmol) is added in one portion to 100 mL of a stirred ice-cold 50% aqueous NaOH solution. Iodomethane (33.0 g, 232.8 mmol) is added dropwise under vigorous stirring to the clear benzimidazole solution at ambient temperature. After 1 h the solution is extracted three times with 100 mL portions of chloroform. The combined organic phases are dried with Na2SO4 and the solvent is removed under reduced pressure. The residue is distilled in vacuo, yielding N-methyl-benzimidazole as a colorless liquid, which solidifies upon cooling. Yield: 21.0 g (75%), mp. 61 C. Elemental anal. % (calc. for C8H8N2): C, 72.50 (72.70); H, 6.19 (6.10); N, 21.18 (21.20).

The synthetic route of 51-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Peppel, Tim; Hinz, Alexander; Koeckerling, Martin; Polyhedron; vol. 52; (2013); p. 482 – 490;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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