Month: April 2021

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 13275-42-8 as follows. Recommanded Product: 2-(2-Bromophenyl)-1H-benzo[d]imidazole

General procedure: Equimolar quantity of 2-(2-bromophenyl)-1H-benzo[d] imidazole (2) and aniline derivatives in 45 ml of 1,4-dioxan was refluxed for 14 hr with continuous stirring at 80. The completion of reaction was checked by TLC. The reaction mixture was kept overnight in a refrigerator. The solvent was evaporated and a gummy solid mass was obtained. The gummy solid was then washed with cold water and recrystallized from ethanol and water (4:6) to obtain the compounds (3a-3h).

According to the analysis of related databases, 13275-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singh, Aruna Chandra; Mittal, Nitin; Pathak, Devender; Indian Journal of Heterocyclic Chemistry; vol. 23; 3; (2014); p. 225 – 232;,
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

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

Adding a certain compound to certain chemical reactions, such as: 101184-08-1, name is Methyl 4-(1H-imidazol-1-yl)benzoate, 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 101184-08-1, Quality Control of Methyl 4-(1H-imidazol-1-yl)benzoate

EXAMPLE 228 1-(Hydroxymethyl)-4-(1H-imidazol-1-yl)benzene To a mixture of 4-(1H-imidazol-1-yl)benzoic acid methyl ester (prepared as described in U.S. Pat. No. 4,804,662) (1.5 g) in THF (25 ml) at -15 C. was added a solution of 1M LAH/THF (10.4) ml). The mixture was stirred for 1/2 hour and allowed to warm to room temperature. The reaction was quenched by addition of water (0.5 ml), and then diluted with methanol (50 ml) and filtered. Concentration of the filtrate yielded 1.2 g (98%) of 1-(hydroxymethyl)-4-(1H-imidazol-1-yl)-benzene.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Merck & Co., Inc.; US5206240; (1993); 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. 116343-89-6, name is Methyl 1-phenyl-1H-imidazole-4-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl 1-phenyl-1H-imidazole-4-carboxylate

To a stirred solution of methyl 1-phenyl-1H-imidazole-4-carboxylate (0.450 g, 2.23 mmol) in THF:water (9:1; 10 ml) was portion wise added NaOH (0.267 g, 6.68 mmol) at 0C. The reactionmixture was stirred at rt for 16 h. The resulting mixture was diluted with ice cold water (60 ml) and acidified using 1 M HC1 solution. The resulting mixture was extracted with EtOAc (3 x 60 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure yielding 1-phenyl-1H-imidazole-4-carboxylic acid (0.230 g, 1.22 mmol). This material was directly used in the next step withoutfurther purification. LCMS: Method C, 1.357 mi MS: ES+ 189.20.

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; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; STOCKLEY, Martin Lee; MADIN, Andrew; (95 pag.)WO2017/103614; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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

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. 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C4H3F3N2

Example 153 1,3,3-Trimethy1.6 [4..(trifluoromethyl)imidazol.. 1y1]indo1in2..one A suspension of 6-bromo-i,3,3-trimethylindolin-2-one (example la, 25.0 mg, 0.098 mmol), 4- (trifluoromethyl)-1H-imidazole (20.094 mg, 0.148 mmol) and potassium carbonate (40.8 mg,0.295mmo1) in acetonitrile (2.Oml) in a microwave tube was sparged with argon for 5 minutes. Then Cul (3.749 mg, 0.02 mmol) and N,N?-dimethylethane-i,2-diamine (0.0040 ml, 0.034 mmol) were added and degas sing was repeated. The tube was sealed and the reaction mixture was heated to 90C under microwave irradiation. The reaction mixture was concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 1 M aqueous HC1 solution. Theorganic layer was dried with sodium sulfate, filtered and the obtained solution concentrated in vacuo. The crude material was purified by silica gel chromatography using hexane/ ethyl acetate as eluent. The title compound was obtained as off-white solid (10 mg).MS ESI (m/z): 310.2 [(M+H)i

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 33468-69-8.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methyl-1H-imidazole

To a solution of 5-bromo-1-methylimidazole (0.68 g, 4.26 mmol) in dry DCM (15 mL), DIPEA (0.77 mL, 4.47 mmol) and iPrMgCl (2.13 mL, 4.26 mmol, 2.0 M solution in THF) was added at 10 C. The reaction mixture was stirred for 1.5 h and a solution of compound J (0.5 g, 1.06 mmol) in DCM was added to it. The reaction mixture was refluxed for 2 h and quenched with saturated NH4Cl solution. The product was extracted with DCM (30 mL). The organic layer was dried, filtered and concentrated to give crude c. Purification of the crude product provided 210 mg (36%) of compound K.1H NMR (400 MHz, CDCl3): delta 0.27 (s, 9H), 3.38 (s, 3H), 3.78 (s, 3H), 6.28 (s, 1H), 6.64 (s, 1H), 7.11 (d, J=7.6 Hz, 1H), 7.22 (s, 1H), 7.24 (s, 1H), 7.29 (s, 1H), 7.30-7.36 (m, 3H), 7.37 (s, 1H), 7.53 (d, J=7.6 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H), 8.57 (d, J=5.0 Hz, 1H); LCMS m/z: 553 (M+1).

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 1003-21-0.

Reference:
Patent; Link Medicine Corporation; US2010/130540; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, 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.

3-[2-(aminomethyl)-5-chlorophenyl]propanoic acid hydrochloride a125 (0.54 g, 2.16 mmol), EtbetaN (1.8 ml_, 13.0 mmol), and trimethylorthoformate (0.30 ml_, 2.16 mmol) are added under stirring and prevention from entrance of air moisture to a solution of 1-trityl-1 H- imidazole-4-carbaldehyde (0.73 g, 2.16 mmol) in absolute methanol (76 ml_), and the mixture is stirred at room temperature for 16 h. NaBH4 (0.13 g, 3.45 mmol) is added, and the mixture is stirred for 1 h and quenched by the addition of a saturated NaHCtheta3 solution to pH 5-6. The solvents are removed under reduced pressure, and the obtained mass is subjected to extraction with ethyl acetate. Water is added to the residue, and undissolved residue is separated by filtration and dried to give 3-[5-chloro-2-({[(1-trityl-1 H-imidazol-4- yl)methyl]amino}methyl)phenyl]propanoic acid a128 (0.71 g). The organic extract is dried over anhydrous Na2SO4 and evaporated to give additionally intermediate a128 (0.40 g).The total yield of intermediate a128 is 1.11 g. Yield: 96 %.1 H NMR deltaH (DMSO, ppm): 2.48 (m, 2 H), 2.81 (t, J = 7.6 Hz, 2 H), 3.86 (s, 2 H), 3.93 (s, 2H), 6.96 (s, 1 H), 7.10 (m, 6 H), 7.20-7.48 (m, 13 H).

The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2008/132139; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 3584-66-5,Some common heterocyclic compound, 3584-66-5, name is 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole, molecular formula is C8H4Cl4N2, 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.

0.5 g of 2-trichloromethylbenzimidazole 3a-m was introduced in portions at 0C into 30 ml of 2N NaOH solution. The resulting solution was acidified (pH 3) using 2N HCI solution and stirred for 1 hour. The mixture was cooled, and the resulting precipitate was filtered off with suction and washed 2 x with WATER/ACETONITRILE (3: 1) and 2 x with diethyl ether. 4a: R = 5-Cl ; brown solid, yield: 97%

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

Reference:
Patent; MERCK PATENT GmbH; WO2005/4863; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem