Category: 6478-79-1

Reference of 6478-79-1, 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 6478-79-1 as follows.

To a solution of compound 1 (0.010?mol) in dry acetone, K2CO3 (0.025?mol) was added and the mixture was stirred at room temperature for 20?min. Then, methyl bromoacetate (0.011?mol) was added to the mixture and stirred at room temperature for one night. Afterwards, the reaction was completed (monitored by TLC, ethylacetate/hexane, 3:1). The product was precipitated by addition of water. It was filtrated off, and recrystallized from ethanol/water, 1:2. Yield: 92%, mp: 166-167?C. 1H NMR (DMSO-d6) ppm: 1.20 (3H, t, J?=?6.8?Hz, CH3), 2.44 (3H, s, CH3), 4.17 (2H. q, J?=?6.8?Hz, OCH2), 5.20 (2H, s, N-CH2), 7.78 (1H, s, Ar-H), 7.91 (1H, s, Ar-H). 13C NMR (DMSO-d6) ppm: 13.78, 14.42 (CH3), 45.12 (NCH2), 61.90 (OCH3), ArC:[112.25, 119.83, 124.45, 124.64, 135.65, 142.19], 155.72 (C=N), 168.35 (C=O). Anal. calcd. (%) for C12H12Cl2N2O2: C, 50.20; H, 4.21; N, 9.76. Found: C, 50.28; H, 4.26; N, 9.69.

According to the analysis of related databases, 6478-79-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mente?e, Emre; Emirik, Mustafa; Soekmen, Bahar Bilgin; Bioorganic Chemistry; vol. 86; (2019); p. 151 – 158;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole, 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 6478-79-1, Application In Synthesis of 5,6-Dichloro-2-methylbenzimidazole

General procedure: To extend the scope of the 2-methyl-1H-benzimidazole substrates for our cascade reaction, we nextexamined the reaction of 2-fluorobenzonitrile (2a) with a variety of 2-methyl-1H-benzimidazolederivatives 1 under the conditions (Cs2CO3, DMSO, 120 C). The results are shown in Table 2. As shown in Table 2, almost all of the tested combinations successfully produced the desiredbenzimidazo[1,2-a]quinolines 8ba-8la with moderate to good isolated yields, though an undeniableamount of overreaction product 9 was isolated in most entries. Unsymmetrical 1H-benzo[d]imidazolessuch as 1b, 1e, 1f and 1g exist as an equilibrium mixture of their tautomers. Therefore, the SNAr sequenceof our cascade reaction with these substrates theoretically provides a regioisomeric mixture of thecorresponding adducts. Our survey revealed that the regiochemical outcome is highly controlled uponutilizing 1e, 1f and 1g having a substituent at the 4-position to give 8ea, 8fa and 8ga without detectingtheir regioisomers (entries 5-7). However, no reigioselectivity was observed with the cascade reactionwith 1b bearing methyl substituent at the 5-position (entry 2). These results suggest to us that the lesssterically congested nitrogen atom of 1H-benzo[d]imidazoles preferably reacted with 2-fluorobenzonitrile(2a) in the SNAr reaction. 2-Methyl-1H-benzimidazole derivatives 1h, 1i, and 1j, having an electrondonating group (-CH3, -OCH3,-SCH3), reacted with 2a to give 8ha, 8ia, and 8ja in modest yields underthe conditions, respectively (entries 8-10). When the benzimidazoles 1k and 1l possessing an electronwithdrawing group (-CN, -CO2Et) at the 2-methyl group were treated with 2a under the conditions, alarge amount of insoluble unidentified product was produced. In these reactions, the desired cascadeproduct 8la was not detected while the cascade product 8ka was isolated in a modest yield (entries 11 and12). The cascade products 8ka and 8la were obtained in good yields upon replacing Cs2CO3 with K2CO3.(entries 11 and 12). In our SNAr/Knoevenagel cascade reaction with 1k and 1l, we found the Knoevenagelcondensation between aldehydes and the active methylene of 1k and 1l occured preferably to the SNArreaction in the first step, and the desired cascade adducts could not be obtained.14 These comparativeresults indicate that the SNAr reaction occured preferably to the Dieckmann-Thorpe type reaction in thepresent cascade reaction upon fine-tuning the base used.

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Reference:
Article; Kato, Jun-Ya; Ito, Yutaro; Ijuin, Ryosuke; Aoyama, Hiroshi; Yokomatsu, Tsutomu; Heterocycles; vol. 93; 2; (2016); p. 613 – 627;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole, 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. Computed Properties of C8H6Cl2N2

To sodium hydride (300 mg) in DMF at 0 C. was added 5,6-dichloro-2-methylbenzoimidazole (500 mg) in one portion. The mixture was stirred at 0 C. for 15 minutes, followed by addition of ethyl 6-bromohexanoate (0.66 mL). The mixture was stirred at 0 C. for another 15 minutes and then at room temperature for 1 hour. The solution was concentrated to dryness under vacuum and the residue was purified by column chromatography on silica gel to give pale brown solid (0.75 g).

The synthetic route of 5,6-Dichloro-2-methylbenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTIUM, INC.; Mao, Fei; Leung, Wai-Yee; Cheung, Ching-Ying; Hoover, Hye Eun; US9097667; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 6478-79-1, 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. 6478-79-1, name is 5,6-Dichloro-2-methylbenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Triethyl orthoacetate (4.6 g, 1 eq) was added drop wise to a refluxing mixture of 4,5-dichloro-1,2-phenylenediamine (5 g, 1 eq) and a catalytic amount of p-toluenesulfonic acid in toluene (40 mL). The mixture was refluxed for 3 hrs and 5.7 g black solid was collected after evaporation of the solvents under reduced pressure and used directly in the following step without further purification. ESI-MS (m/z) calcd (found): 200.0 (201.1) for [M+H]+. To the crude 5,6-dichloro-2-methyl-benzoimidazole (5.7 g, 1 eq) (see FIG. 9) and grinded potassium hydroxide (4.8 g, 3 eq) in acetone (50 mL) was added iodomethane (5.2 g, 1.4 eq) drop wise and the mixture was stirred overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between dichloromethane (200 mL) and water (200 mL). The aqueous phase was washed two times with dichloromethane (200 mL) and the combined organic phase was dried over Na2SO4 and evaporated to dryness. The crude product was recrystallized from ethyl acetate. 5.5 g product was collected as pale flakes with 90.6% yield for two steps. 1H NMR: (CDCl3) 2.55 (s, 3H), 3.63 (s, 3H), 7.28 (s, 1H), 7.68 (s, 1H). 13C NMR: (CDCl3): 13.82, 30.05, 110.20, 120.00, 125.58, 125.75, 134.97, 141.83, 153.93. ESI-MS (m/z) calcd (found): 214.0 (215.1) for [M+H]+.

The synthetic route of 5,6-Dichloro-2-methylbenzimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; New York University; Chang, Young-Tae; Wang, Shenliang; US8716491; (2014); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem