Tag: M.W=100-200

Synthetic Route of 7152-24-1,Some common heterocyclic compound, 7152-24-1, name is 2-(Methylthio)benzimidazole, molecular formula is C8H8N2S, 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.

EXAMPLES Synthesis of Compound 1 A suspension of 164 g (1.0 mol) of 2-methylthiobenzimidazole (manufactured by Tokyo Kasei Co. or Aldrich Co.) in 1500 ml of water was prepared. To it were added 1.65 g (0.005 mol) of sodium tungstate dihydrate and 280 ml of 35% aqueous hydrogen peroxide. The mixture was placed in a water bath of 50 C. and stirred for 6 hours. During this period, 181 g of 2-methanesulfonylbenzimidazole precipitated and was collected by filtration.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Methylthio)benzimidazole, its application will become more common.

Reference:
Patent; Fuji Photo Film Co., Ltd.; US5097042; (1992); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 4887-80-3,Some common heterocyclic compound, 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole, molecular formula is C8H8N2O, 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.

5-Methoxybenzimidazole (0.50 g, 3.37 mmol) was dissolved in acetonitrile (5 mL), potassium hydroxide (0.39 g, 6.95 mmol) was added, and the mixture was refluxed for 30 min. 2-(Bromomethyl)naphthalene (0.76 g, 3.44 mmol) was added, and the mixture was refluxed overnight.

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

Reference:
Article; Shelton, Kerri L.; DeBord, Michael A.; Wagers, Patrick O.; Southerland, Marie R.; Williams, Travis M.; Robishaw, Nikki K.; Shriver, Leah P.; Tessier, Claire A.; Panzner, Matthew J.; Youngs, Wiley J.; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 421 – 439;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 2403-66-9, name is 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, 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. Quality Control of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol

6-chloro-N-[(2,4-dimethylthiazol-5-yl)methyl]-5-methyl-2-methylsulfonyl-pyrimidin-4-amine F5 (480 mg, 1.384mmol) and 3-(1H-benzimidazol-2-yl)propan-1-ol (244 mg, 1.38 mmol) were placed in a 20 mL vial and dissolved in THF(5 mL). AIM solution of NaHMDS in THF (1.38 mL, 1.38 mmol) was added, and the reaction was stirred overnight.Solvent was then removed, and the product was purified by silica gel flash column chromatography (EtOAc/hexanesgradient). 500 mg (82%) of F6 were isolated as an off-white foam. 1H NMR delta (300 MHz, DMSO-d6): 7.84-7.80 (1 H, m),7.76 (2 H, dd, J = 6.20, 3.18 Hz), 7.51 (2 H, dd, J = 6.28, 3.15 Hz), 4.46 (2 H, d, J = 5.76 Hz), 4.37-4.31 (2 H, m), 2.54(4H, s), 2.46 (3 H, s), 2.29 (3 H, s), 1.99 (3 H, s). HRMS (Electrospray): m/z 443.1413 (MH+).

The synthetic route of 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; COX, Christopher; RAHEEM, Izzat, T.; SHIPE, William, D.; THEBERGE, Cory, R.; (62 pag.)EP2621276; (2017); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 63655-40-3,Some common heterocyclic compound, 63655-40-3, name is 2-Amino-1H-benzo[d]imidazole-5-carbonitrile, molecular formula is C8H6N4, 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.

Benzimidazole based Schiff base 1 is prepared from 2-aminobenzimidazoleand aromatic aldehyde in absolute ethanolfor 12 h at reflux, as reported previously (17). Detailed description can be found in the Supporting Information.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-1H-benzo[d]imidazole-5-carbonitrile, its application will become more common.

Reference:
Article; Horak, Ema; Vianello, Robert; Hranjec, Marijana; Murkovi? Steinberg, Ivana; Supramolecular Chemistry; vol. 30; 10; (2018); p. 891 – 900;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 45676-04-8, The chemical industry reduces the impact on the environment during synthesis 45676-04-8, name is 1-tert-Butylimidazole, I believe this compound will play a more active role in future production and life.

F) 1,1′-Di-tert-butyl-3,3′-methylenediimidazolium diiodide 13 0.008 mol of diiodomethane (2.143 g; 0.64 ml) and 5 ml of tetrahydrofuran are added to 0.016 mol of tertbutylimidazole 2 (2.000 g) in an ACE pressure tube. The reaction mixture is stirred at 80 C. for 3 hours. The precipitated solid is washed repeatedly with a little tetrahydrofuran. The white solid 13 is obtained. Empirical formula: C15H26N4I2 M=516.198 g/mol Yield: 1.444 g (35.0% of theory) Melting point: decomposition at >249 C. 1H (ppm, d6-DMSO, 300.13 MHz): delta=9.55 (s, 2H, NCN); 8.17 (s, 2H, NCCHN); 8.06 (s, 2H, NCHCN); 6.54 (s, 2H, NC2N); 1.61 (s, 18H, C3 group)

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-tert-Butylimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; TECHNISCHE UNIVERSITAET DRESDEN; US2009/326237; (2009); 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. 10597-52-1, name is 7-Nitro-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 7-Nitro-1H-benzo[d]imidazole

To a stirred suspension of benzimidazole 34 (4.11 g, 30.6 mmol) in 230 mL of CH3CN was added BSA (8.22 mL,39.8 mmol), and the solution was stirred for 10 min during which time the reaction mixture became homogenous. TAR (9.65 g, 39.8 mmol) was added followed by TMSOTf (5.88 mL, 38.8 mmol) and the reaction was heated to reflux for 3 h before being cooled to rt and diluted with 200 mL of EtOAc. The organic layer was washed with 200mL of satd. NaHCO3 and 200 mL of brine. The organic layer was then dried (Na2SO4), filtered, and concentrated in vacuo to afford a yellow oil. The oil was purified by flash chromatography (0-20% MeOH/DCM) to afford the triacetate 35

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:
Article; Brockway, Anthony J.; Volkov, Oleg A.; Cosner, Casey C.; MacMillan, Karen S.; Wring, Stephen A.; Richardson, Thomas E.; Peel, Michael; Phillips, Margaret A.; De Brabander, Jef K.; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5433 – 5440;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 29043-48-9, A common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

The synthetic route of 29043-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 17289-26-8, 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. 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

190c) (Z)-tert-Butyl 3-(1 -methyl- -imidazol-4-yl)acrylate To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (9.62 g, 38.1 mmol) in tetrahydrofuran (THF) (50 mL), sodium hydride (1 .831 g, 45.8 mmol) was added. The reaction mixture was stirred at 0 C under N2 for 10 mins. Then a solution of 1 -methyl- 1 H-imidazole-4-carbaldehyde (4.2 g, 38.1 mmol) in THF (50 mL) was added and the reaction mixture was stirred at 0 C for 150 mins. Water (100 mL) was added and extracted with ethyl acetate (3x). The organic layer was washed with water (2x) and brin (2x), dried over Na2S04 and concentrated. The crude product was purified on silica gel chromatography (hexane:ethyl acetate :TEA= 1 :1 :0.01) to afford the title compound (Z)- tert-butyl 3-(1 -methyl-1 H-imidazol-4-yl)acrylate (6.1 g, 28.7 mmol, 75 % yield) as colorless oil. LC-MS m/z 201 .1 (M+H)+, 1 .72 min (ret. time).

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-imidazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 54624-57-6, A common heterocyclic compound, 54624-57-6, name is 2-Bromobenzimidazole, molecular formula is C7H5BrN2, 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.

Sodium hydride (60% dispersion in mineral oil, 0.665 g, 16.63 mmol) was added to a solution of 2-bromo-lH-benzo[d]imidazole (2.73 g, 13.86 mmol) in DMF (30 mL), and the reaction stirred for 10 minutes at ambient temperature. l-Bromo-2-methoxy ethane (1.541 ml, 16.63 mmol) was added, and reaction stirred overnight at ambient temperature. The reaction was diluted with ethyl acetate and washed several times with brine. The organic layer was separated and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified via column chromatography on a 100 gram silica gel column eluting with 20-40%) ethyl acetate- hexane. The desired fractions were combined and concentrated to afford 2-bromo-l-(2- methoxyethyl)-lH-benzo[d]imidazole (2.9 g, 82%) as an orange oil. 1H NMR (300 MHz, DMSO-i) delta ppm 7.54 – 7.67 (m, 2 H) 7.14 – 7.34 (m, 2 H) 4.42 (t, j=5.28 Hz, 2 H) 3.67 (t, J=5.28 Hz, 2 H) 3.20 (s, 3 H).

The synthetic route of 54624-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 111851-98-0,Some common heterocyclic compound, 111851-98-0, name is 1-Ethyl-1H-imidazole-2-carbaldehyde, molecular formula is C6H8N2O, 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.

To a refluxing solution of propionic acid (450 mL) and 1-ethylimidazole-2-carboxaldehyde (62, 2.5 g, 20.0 mmol, prepared in a similar manner as the methyl imidazole derivative 20) was added pyrrole (1.40 mL, 20.0 mmol). The reaction was covered in foil then heated under reflux for 5 h. Upon cooling, the reaction mixture was exposed to air overnight. The propionic acid was then removed by vacuum distillation. Repeated purification by column chromatography (gradient elution, CHCl3/MeOH/concentrated NH4OH/EtOAc) provided porphyrin 63 as a purple solid (281 mg, 8.1%): 1H NMR (300 MHz, CDCl3) delta -2.95, -2.90, -2.87 (3 s, 2 H, atropisomer NH), 0.85-1.25 (multiple t, 12 H, atropisomer CH3), 3.61-3.88 (multiple q, 8 H, atropisomer CH2), 7.55 (d, 4 H), 7.70 (d, 4 H), 8.98 (multiple s, 8 H, atropisomer).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Ethyl-1H-imidazole-2-carbaldehyde, its application will become more common.

Reference:
Patent; Aeolus Sciences, Inc.; National Jewish Health; Duke University; Crapo, James D.; Day, Brian J.; Trova, Michael P.; Gauuan, Polivina Jolicia F.; Kitchen, Douglas B.; Fridovich, Irwin; Batinic-Haberle, Ines; (44 pag.)US9289434; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem