Category: 614-97-1

Application of 614-97-1, A common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methyl-1H-benzo[d]imidazole (2.0 g, 15.13 mmol), triethylamine (5.27 mL, 37.8 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (5.27 mL, 22.70 mmol). The reaction mixture was stirred overnight at room temperature, and the resulting solution was diluted with water (30 mL), extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried, filtered, and concentrated under vacuum to afford a mixture of tert-butyl 5-methyl- 1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-methyl-1H-benzo[d]imidazole-1- carboxylate (3.12 g) as a yellow oil. LCMS m/z = 177.1 [M+H-isobutylene]+.

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, 5-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

614-97-1, name is 5-Methyl-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. Formula: C8H8N2

General procedure: A sealable reaction tube equipped with a magnetic stirrer barwas charged with 5,6-dimethyl-1H-benzo[d]imidazole (0.50 mmol,73 mg), benzaldehyde (1.0 mmol, 106 mg), di-tert-butyl-peroxide(1.0 mmol, 146 mg), 4 A molecular sieves (50 mg) and ethyl acetate(3.0 mL). The rubber septum was then replaced by a Teflon-coatedscrew cap, then the reaction must be under N2 and the reactionvessel placed in an oil bath at 110 C. After stirring the mixture atthis temperature for 15 h, it was cooled to room temperature anddiluted with ethyl acetate then washed with 0.5 mmol/L NaOHaqueous solution (5.0 mL3), dried over by MgSO4. After the solventwas removed under reduced pressure, the residue was purifiedby column chromatography on silica gel (hexane/EtOAc, 4:1 to6:1) to afford the desired product (5,6-dimethyl-1H-benzo[d]imidazol-1-yl)(phenyl)methanone (3a, 116 mg, 93% yield).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Lin; Wang, Min; Wang, Lei; Tetrahedron; vol. 70; 35; (2014); p. 5391 – 5397;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 614-97-1,Some common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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 solution of 5-methyl-1H-benzo[d]imidazole (2.0 g, 15.13 mmol), triethylamine (5.27 mL, 37.8 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (5.27 mL, 22.70 mmol). The reaction mixture was stirred overnight at room temperature, and the resulting solution was diluted with water (30 mL), extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried, filtered, and concentrated under vacuum to afford a mixture of tert-butyl 5-methyl- 1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-methyl-1H-benzo[d]imidazole-1- carboxylate (3.12 g) as a yellow oil. LCMS m/z = 177.1 [M+H-isobutylene]+. To a solution of a mixture of tert-Butyl 5-methyl-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6- methyl-1H-benzo[d]imidazole-1-carboxylate(1.0 g, 4.31 mmol) and NBS (0.766 g, 4.31 mmol) in CCl4 (30 mL) stirred under nitrogen at room temperature was added AIBN (0.071 g, 0.431 mmol). The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature, washed with water (3 x 50 mL), and concentrated to afford a mixture of tert-butyl 5-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6- (bromomethyl)-1H-benzo[d]imidazole-1-carboxylate (0.7 g) as a yellow oil. LCMS m/z = 211.0 [M+H-boc]+. To a solution of 4-ethyl-2-mercapto-6-(4-methyl-1,4-diazepan-1-yl)pyridine-3,5- dicarbonitrile (synthesis described in example 69 step 1, 581 mg, 1.93 mmol) and triethylamine (488 mg, 4.82 mmol) in DMF (20 mL) was added a mixture of tert-butyl 5- (bromomethyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-(bromomethyl)-1H- benzo[d]imidazole-1-carboxylate (600 mg, 1.93 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into 20 mL of water. The resulting solution was extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with brine and water, then dried and concentrated. The residue was purified by silica gel column (0-50% ethyl acetate in hexane) to afford a mixture of tert-butyl 5-(((3,5- dicyano-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H- benzo[d]imidazole-1-carboxylate and tert-butyl 6-(((3,5-dicyano-4-ethyl-6-(4-methyl-1,4- diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H-benzo[d]imidazole-1-carboxylate (410 mg, 0.77 mmol) as a yellow solid. LCMS m/z = 532.1 [M+H]+. To a mixture of tert-butyl 5-(((3,5- , pan-1-yl)pyridin-2- yl)thio)methyl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-(((3,5-dicyano-4-ethyl- 6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl)thio)methyl)-1H-benzo[d]imidazole-1- carboxylate (430 mg, 0.81 mmol) in DCM (5.0 mL) was added trifluoroacetic acid (5.0 mL), then the reaction mixture was stirred overnight at room temperature. The residue was diluted with water, then adjusted to pH 13 with Na2CO3. The resulting solution was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum. The residue was purified by silica gel column (50% ethyl acetate n hexane) to afford 2-(((1H- benzo[d]imidazol-5-yl)methyl)thio)-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridine-3,5- dicarbonitrile (310 mg, 0.71 mmol) as a yellow oil. LCMS m/z = 432.1 [M+H]+.1H NMR (400 MHz, MeOD) delta ppm 8.18 (s, 1H), 7.67 (s, 1H), 7.59 (d, J = 8.3 Hz, 1H), 7.34 (d, J = 8.3 Hz, 1H), 4.65 (s, 2H), 3.97 (d, J = 4.8 Hz, 4H), 2.95- 2.86 (m, 2H), 2.71- 2.63 (m, 2H), 2.62- 2.56 (m, 2H), 2.28 (s, 3H), 2.09-1.99 (m, 2H), 1.32 (t, J = 6.1 Hz, 3H).

The synthetic route of 614-97-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Equimolar quantities of the 7-bromo alkane derivatives (2a-2c) and corresponding benzimidazole were dissolved in acetone (30 mL), and certain amount of K2CO3 was also added to the solution. The solution was then refluxed for approximately 12 h. The product was extracted by dichloromethane. Then evaporated of the solvent, the residue was purified bycolumn chromatography on silica gel, eluting with dichloromethane/methanol (30:1) to givethe compounds 3-23.

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, 5-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article in Press; Wang, Zhe; Deng, Xiangping; Xiong, Shujuan; Xiong, Runde; Liu, Juan; Zou, Liu; Lei, Xiaoyong; Cao, Xuan; Xie, Zhizhong; Chen, Yanming; Liu, Yunmei; Zheng, Xing; Tang, Guotao; Natural Product Research; (2017); p. 1 – 10;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Equimolar quantities of the 7-bromo alkane derivatives (2a-2c) and corresponding benzimidazole were dissolved in acetone (30 mL), and certain amount of K2CO3 was also added to the solution. The solution was then refluxed for approximately 12 h. The product was extracted by dichloromethane. Then evaporated of the solvent, the residue was purified bycolumn chromatography on silica gel, eluting with dichloromethane/methanol (30:1) to givethe compounds 3-23.

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, 5-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article in Press; Wang, Zhe; Deng, Xiangping; Xiong, Shujuan; Xiong, Runde; Liu, Juan; Zou, Liu; Lei, Xiaoyong; Cao, Xuan; Xie, Zhizhong; Chen, Yanming; Liu, Yunmei; Zheng, Xing; Tang, Guotao; Natural Product Research; (2017); p. 1 – 10;,
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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8N2

General procedure: To a stirred solution of copper(I) acetate (2.4 mg, 0.020 mmol, 0.10 equiv.), benzimidazole 1a (23.6 mg, 0.20 mmol), and TMP iodonium(III) salt 2a (124.8 mg, 0.24 mmol, 1.2 equiv) in toluene (2 mL), triethylamine (56 mL, 0.4 mmol, 2 equiv) was added under a nitrogen atmosphere. The mixture was stirred for 5 min at room temperature, and the resulting solution was then heated to 50 C for 6 h (the reaction progress was monitored by TLC). After cooling to room temperature, the reaction was quenched by adding 5% aqueous ammonia solution (4 mL). The aqueous layer was extracted thrice with 20 mL of dichloromethane and the combined organic extracts were dried with anhydrous sodium sulfate. The organic solvents were then evaporated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 1/1) to obtain pure N-phenyl benzimidazole 3aa (38.5 mg, 0.198 mmol) in 99% yield

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; Koseki, Daichi; Aoto, Erika; Shoji, Toshitaka; Watanabe, Kazuma; In, Yasuko; Kita, Yasuyuki; Dohi, Toshifumi; Tetrahedron Letters; vol. 60; 18; (2019); p. 1281 – 1286;,
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

Related Products of 614-97-1, 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. 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methyl-1H-benzo[d]imidazole (2.0 g, 15.13 mmol), triethylamine (5.27 mL, 37.8 mmol) in dichloromethane (30 mL) was added di-tert-butyl dicarbonate (5.27 mL, 22.70 mmol). The reaction mixture was stirred overnight at room temperature, and the resulting solution was diluted with water (30 mL), extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried, filtered, and concentrated under vacuum to afford a mixture of tert-butyl 5-methyl- 1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-methyl-1H-benzo[d]imidazole-1- carboxylate (3.12 g) as a yellow oil. LCMS m/z = 177.1 [M+H-isobutylene]+.

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, 5-Methyl-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Nicholas David; BENOWITZ, Andrew B.; RUEDA BENEDE, Maria Lourdes; EVANS, Karen Anderson; FOSBENNER, David T.; KING, Bryan Wayne; LI, Mei; MILLER, William Henry; REIF, Alexander Joseph; ROMERIL, Stuart Paul; SCHMIDT, Stanley J.; WIGGALL, Kenneth; (1283 pag.)WO2017/216726; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[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. category: imidazoles-derivatives

General procedure: Equivalent amount of the N-protected amino acid or dipeptide (1.45 mmol) (2a: 300 mg, 2b: 320 mg, 2c: 440 mg, 2d: 480 mg, 2e: 250 mg, 2f: 390 mg, 2g: 300 g, 2h: 440 mg, 2i: 250 mg, 2j: 390 mg, 2k: 300 mg, 2l: 320 mg, 2m: 440mg, 2n: 480 mg, 2o: 390 mg, 2p: 520 mg), benzimidazole (or its derivative) (1.45 mmol), (2a, 2b, 2c, 2d, 2e, 2f: 170mg, 2g, 2h, 2i, 2j: 190 mg, 2k, 2l, 2m, 2n, 2o: 240 mg, 2p:170 mg) and DCC (300 mg, 1.45 mmol) were reacted in dried THF (10 mL) under an atmosphere of argon for 3 h at room temperature and formed dicyclohexzylurea was filtered off. The volatiles were removed with reduced pressure. The residue was crystallized from ethanol/diethyl ether (1:2) (Fig. 1).

The synthetic route of 5-Methyl-1H-benzo[d]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bu?day, Nesrin; Kuecuekbay, F. Zehra; Apohan, Elif; Kuecuekbay, Hasan; Serinda?, Ayfer; Ye?ilada, Oezfer; Letters in Organic Chemistry; vol. 14; 3; (2017); p. 198 – 206;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem