Tag: M.W=200-300

Application of 68468-39-3, 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. 68468-39-3, name is 5-Bromo-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,4-Dinitrochlorobenzene (1 mmol), 2-mercapto-5-substituted benzimidazoles (1 mmol) and Potassium hydroxide (1 mmol) were suspended in aqueous-EtOH (1:1). The reaction mixture was stirred vigorously for about 30 minutes and then refluxed on water bath for 2.5 h, at which point it cleared and TLC analysis indicated complete consumption of the reactants. The reaction mixture was diluted with 50 mL of water and cooled in ice, and the precipitate was collected by filtration. After being washed with cold water (2 x 25 mL), the precipitate was dried under vacuum to afford a pure product (3a-d).

The synthetic route of 5-Bromo-1H-benzo[d]imidazole-2(3H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kankala, Shravankumar; Kankala, Ranjith Kumar; Gundepaka, Prasad; Thota, Niranjan; Nerella, Srinivas; Gangula, Mohan Rao; Guguloth, Hanmanthu; Kagga, Mukkanti; Vadde, Ravinder; Vasam, Chandra Sekhar; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1306 – 1309;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 129378-52-5,Some common heterocyclic compound, 129378-52-5, name is 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, molecular formula is C11H23N3O2SSi, 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.

Intermediate 26: 4(5)-Chloro-1 H-imidazoleHO. alphaTo a solution of 2-[(1 ,1-dimethylethyl)(dimethyl)silyl]-N,N-dimethyl-1 H-imidazole-1- sulfonamide (for preparation see US2005075366,15 g, 51.8 mmol) in dry THF (100 ml_), under nitrogen and at -7O0C, a 1.6M solution of butyllithium in hexane (34.0 ml_, 54.4 mmol) was slowly added. The temperature was allowed to reach -550C in 1 hour then cooled down to -780C and dimethylsulfamoyl chloride (8.33 ml_, 78 mmol) was slowly added and the mixture was stirred at -780C for 30min and at 2O0C for 2 hours. The solvents were removed by evaporation and the residue was stirred with 2M HCI solution (100ml) for 12 hour at room temperature. Complete deprotection of the nitrogen was achieved while partial TBDMS deprotection was observed. The aqueous acid solution was basified with KOH pellets and the aqueous phase was extracted with EtOAc. The organic phases were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was treated with a 1 M solution of TBAF in THF (51.8 ml_, 51.8 mmol) and heated to 6O0C for 2 hours. The volatiles were removed under vacuo and the residue was chromatographed to give the title compound (3.5 g, 34.1 mmol); UPLC/MS Rt=O.33 min; m/z (ES): 103 and 105 [M+H]+; 1H NMR (CDCI3): delta 7.00 (d, 1 H), 7.57 (d, 1 H), 11.54 (brs, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 60713-78-2, A common heterocyclic compound, 60713-78-2, name is 5-Chloro-6-nitro-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C7H4ClN3O3, 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.

To 5-chloro-6-nitro-1 ,3- dihydro-benzoimidazol-2-one (5.63 g, 26.35 mmol) was added phosphorus oxychloride (35 ml_) and the reaction mixture was heated to 85 0C for 36 h. The reaction mixture was concentrated and the residue triturated with cold saturated aqueous sodium bicarbonate (to pH 8, 0.8 L). The resulting precipitate was collected and dried to yield the titled compound (5.43 g, 89% yield). MS (ESI/CI): mass calcd. for C7H3CI2N3O2, 231.0; m/z found, 232.0 [M+H]+. Step C: 2,6-Dichloro-1 -(2-methoxy-ethoxymethyl)-5-nitro-1 /-/-benzoimidazole.

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; JANSSEN PHARMACEUTICA NV; WO2009/134750; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

78597-27-0, name is 6-Iodo-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. Recommanded Product: 6-Iodo-1H-benzo[d]imidazole

To a solution of (4-(3 -ethynylimidazo [1,2 -bjpyridazin-6-yl)phenyl)(4-methylpiperazin- 1- yl)methanone (30 mg, 0.089 mmol), and 5-iodo-1H-benzo[djimidazole in a mixture of THF and DMF (2:1, 1.5 mL) was added PdC12(PPh3)2 (3.0 mg, 0.004 mmol), Cul (1.6 mg, 0.0086 mmol), Et3N (1 mL) and then the reaction mixture was stirred? at room temperature for 12 h. The reaction mixture was concentrated in vacuo to dryness and the residue was purified by column chromatography (silica gel, eluent CH2C12/MeOH 95:5-9O: 10) to afford (4-(3-((1H- benzo [di imidazol-5-yl)ethynyl)imidazo [1 ,2-bjpyridazin-6-yl)phenyl)(morpholino)methanone (90 mg, 67%, AUC HPLC 99%) as a yellow solid. ?H NMR (400 MHz, DMSO-56) 5 (ppm):8.35 (s, 1H), 8.32 (d, J= 9.5 Hz, 1H), 8.21 (d, J= 8.4Hz,2H),8.20(s, 1H), 7.96(d, 1=9.5Hz, 1H),7.91 (s, 1H), 7.70(d, 1= 8.2Hz, 1H), 7.63 (d, J= 8.4 Hz, 2H), 7.49 (dd, J= 8.2, 1.2 Hz, 1H),3.79-3.32 (m, 8H); ?3C NMR (100 MHz, DMSO-d6) 5 (ppm: 168.52, 151.31, 143.81, 138.66,138.31, 137.19, 135.74, 127.84, 127.13, 126.34, 125.42, 117.50, 114,82, 112.69, 99.59,74.78, 66.04, 47.66; MS (ESI) mlz 449 [C26H20N602+Hjt

The synthetic route of 78597-27-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH (A*STAR); NACRO, Kassoum; CHENNAMANENI, Lohitha Rao; (62 pag.)WO2019/13703; (2019); 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. 256518-97-5, name is 2-Chloro-5-iodo-1H-benzo[d]imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 256518-97-5

2-Chloro-6-iodo-1H-benzimidazole (2.34 g, 8.4 mmol) was added to the reaction vessel under nitrogen atmosphere.Isopropyl boric acid (0.81 g, 9.2 mmol),Tetrakistriphenylphosphine palladium (0.09g, 0.08mmol),Potassium carbonate (3.48g, 25.2mmol),Toluene 60mL, ethanol 20mL and distilled water 20mL,Stir at 120 C for 3 h.After the end of the reaction, the reaction was quenched with distilled water, extracted with ethyl acetate, and the organic layer was dried over MgSO 4After purification by silica gel column chromatography, Intermediate 21-3 (1.23 g, 75%) was obtained

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 256518-97-5.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (20 pag.)CN108727274; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 65039-05-6 as follows. category: imidazoles-derivatives

Add to a 100 mL round bottom flaskGlyphosate 1.69g (10mmol),Methanol (40 mL) and potassium hydroxide 0.62 g (11 mmol),Magnetic stirring at 50C,After the reaction solution is clarified,1-butyl-3-methylimidazolium iodide 2.66 g (10 mmol) was added,The reaction was stirred at room temperature for 0.75 hours.Dichloromethane (3 x 20 mL) was added for extraction.After the extraction is completed,The organic phase is washed once with saturated saline solution.Distilled and washed onceRotary evaporation,And dried in a vacuum drying oven to give a yellow oily liquid,Yield 90%.

According to the analysis of related databases, 65039-05-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang Academy Of Agricultural Sciences; Yu Jianzhong; He Hongmei; Zhang Changpeng; Xu Zhenlan; Wu Min; Zhang Chunrong; He Kaiyu; Zhu Yahong; Yu Ruixian; Zhao Hua; (8 pag.)CN107987104; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 5851-49-0, A common heterocyclic compound, 5851-49-0, name is 2-Heptyl-1H-benzo[d]imidazole, molecular formula is C14H20N2, 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.

2-Heptyl-benzimidazole (0.09 g, 0.42 mmol) was dissolved in acetonitrile (5 mL), potassium hydroxide (0.03 g, 0.53 mmol) was added and the mixture was refluxed for 30 min. 2-(Bromomethyl)naphthalene (0.11 g, 0.50 mmol) was added and the mixture was refluxed overnight.

The synthetic route of 5851-49-0 has been constantly updated, and we look forward to future research findings.

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

Application of 78597-27-0, A common heterocyclic compound, 78597-27-0, name is 6-Iodo-1H-benzo[d]imidazole, molecular formula is C7H5IN2, 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.

b) 5-((Trimethylsilyl)ethynyl)- 1 H-benzo [djimidazoleA solution of of the compound of Intermediate Example 12(a) (0.7 g, 2.56 mmol) inDMF-Et3N (1:1; 10 ml) was degassed by N2 bubbling for 15 mm. Pd(dppf)Cl2 (0.11g,. 0.14. mmol, 0.05 eq), copper(]) iodide (0.054g, 0.25 mmol, 0.1 eq) and ethynyltrimethylsilane.(0.3 g, 3.15 mmol; 1.1 eq) were added sequentially and the mixture was stirred for 12 h at RT. The mixture was quenched and extracted as in Intermediate Example 1. The solvent was distilled off and the crude residue was recrystallized fromhexane to afford the title product in 57 % yield (0.35 g). LC-MS (ESI): Calculated mass:214.09;Observed mass: 215.5 jM+H] + (rt: 0.22 mm).

The synthetic route of 78597-27-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; RAJAGOPALAN, Srinivasan; APPUKUTTAN, Prasad; NARASINGAPURAM ARUMUGAM, Karthikeyan; UJJINAMATADA, Ravi Kotrabasaiah; GEORGE, Shyla; LINNANEN, Tero; WO2014/162039; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 92807-02-8, The chemical industry reduces the impact on the environment during synthesis 92807-02-8, name is Methyl 2-mercapto-1H-benzo[d]imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Example 42: [2- (4-ACETYLAMINO-BENZVLSULFANYL)-1 H-BENZIMIDAZOLE-4-CARBOXYLIC ACID] amide (42) (a) [2- (4-ACETYLAMINO-BENZYLSULFANYL)-1 M-BENZIMIDAZOLE-4-CARBOXYLIC ACID METHYL] ester [0135] A solution containing 85 mg of [2-MERCAPTO-1 H-BENZIMIDAZOLE-4-CARBOXYLIC] acid methyl ester (0.40 [MMOL)] in 4 mL DMF was cooled to 0 [C.] To this was added 130 mg CsCO3 (0.40 [MMOL)] followed by 91 mg of [4-ACETAMIDOBENZYL] chloride (0.49 [MMOL).] The reaction was stirred overnight, allowing it to warm to 23 C, and then concentrated in vacuo. The resulting crude material was suspended in pH 7 buffer and extracted with EtOAc (x3). The combined organic layers were dried [(MGS04),] filtered and concentrated. Purification by flash silica gel chromatography using a gradient solvent system (80% EtOAc/Hex to 100% EtOAc) gave 112 mg of product (0.31 mmol, 77%) as a colorless oil that crystallized upon standing. [0136] IR (KBr) 3283,3196, 1732,1709, 1666,1602, 1547,1514, 1448,1431, 1412, 1350,1302, 1297,1203, 1145,1124, [754 CM-1. 1H NMR (CDCL3) No. 2. ] 16 (s, 3H), 3.97 (s, [3H),] 4.56 (s, 2H), 7.23-7. 29 (m, 1 H), 7.36-7. 47 (m, 4H), 7.82 (d, [1 H, J = 7.] 7 Hz), 7.87 (d, 1 H, J = 7.7 Hz), 10.16 (br s, 1 H), not seen 1 H (NH). HPLC Rt = 5.643 min. [ANAL. (C18HL 7N303S)] C, H, N, S.

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, Methyl 2-mercapto-1H-benzo[d]imidazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2003/106430; (2003); A1;,
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