Category: 615-16-7

Application of 615-16-7,Some common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, molecular formula is C7H6N2O, 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 three flask equipped with a thermometer dichloroethane solvent 1000ml, added slowly with stirring 268gBenzimidazolone. Meanwhile weighed 305g of fuming nitric acid (concentration ?95%), and slowly poured three bottles, while down while stirring. Then added phosphorus pentoxide 20g. Reflux, the reaction temperature is 85 , TLC tracking dinitro compound detected is generated to stop the reaction. While recovering the solvent was concentrated under reduced pressure, water was added, extraction dichloroethane, and the solvent was evaporated to dryness to give the product recovered organic phase was dried over anhydrous sodium sulfate. 381g dried to give a solid, a yield of 85.1%.

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

Reference:
Patent; Qingdao Huangdao Hospital of Traditional Chinese Medicine; Lu, Yanmin; (5 pag.)CN105732510; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 615-16-7, 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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 23; Preparation of 3-((2-(l,3-dimethyl-2-oxu-2)3-dihydro-l//-benzimidazol-5-yl)-2- oxoethyl)tbio) propanoic acid (23); (i) l,3-Dimethyl-l,3-dihydro-2W-bcn7.iitauiidazol-2-onc; l,3-Dihydro-2H-benziiuida7;ol-2-one (7.522 g, 56.1 mmol) was dissolved in anhydrous DIvIF (125 oil) and anhydrous potassium carbonate (46.581 g, 337 mmol) and iodomethane (21 ml, 337 mmol) were added then the mixture stirred at room temperature overnight. The reaction mixture was poured into chloroform (500 ml), filtered and the filtrate was evaporated to dryness. The resultant residue was dissolved in a mixture of ethyl acetate (150 ml) and water (100 ml). The cthyi acetate phase was washed with water (2 x 100 ml) and brine ( 100 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to dryness to give the title compound (7,229 g, 79% yield) as a pale yellow solid.1H nmr (400 MHz1 CDCl3) delta 3.43 (s, 6H); 6.95-7.01 (m, 2H); 7.08-7.14 (m, 211).

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, 2-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CORTICAL PTY LTD; WO2007/70961; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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 a solution of benzimidazole-2-one (Aldrich, 1.1 g, 7.5 mmol) in DMF (20 ml) was added 3,6-dichlorobenzoisoxazole (1.5 g, 7.5 mmol) and Cs2CO3 (4.8 g, 15 mmol). The suspension was heated to 15O0C in an oil bath and stirred overnight. The mixture was then cooled to room temperature, diluted with water (30 ml) and stirred in a ice bath for 2 hours. The mixture was then filtered. The solid was washed with water and dried under high vacuum to obtain 2.0 g (93%) of a yellow solid as l-(6-chlorobenzisoxazol-3-yl)benzimidazole-2-one. To a solution of the above product (1.0 g, 3.5 mmol) in DMF (15 ml) was added NaOMe solution in methanol (30% wt/wt, 10 ml). The mixture was heated to 8O0C under vacuum to remove residual methanol and then stirred at 11O0C under nitrogen overnight. The mixture was then cooled to room temperature, diluted with water (50 ml), adjusted to pH 6 with 10% aqueous HCl. The resulting suspension was stirred in an ice bath for 2 hours and filtered. The solid was washed with water and dried in an oven (900C) for 2 hours and then under high vacuum at room temperature for 3 hours to obtain a slightly yellow solid. LC-MS m/e: (M+ 1) = 282

Statistics shows that 2-Hydroxybenzimidazole is playing an increasingly important role. we look forward to future research findings about 615-16-7.

Reference:
Patent; MERCK & CO., INC.; WO2006/22954; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 615-16-7, These common heterocyclic compound, 615-16-7, name is 2-Hydroxybenzimidazole, 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 a stirred solution of compound 114 (1 g, 7.46 mmol) in CH2C12 (10 mL) under argon atmosphere was added chlorosulfonic acid (1 mL, 14.92 mmol) at 0 C; heated to reflux and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo and the residue diluted with water (10 mL); neutralized with aqueous NaOH solution and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 115 (980 mg, 58%) as an off-white solid. TLC: 10% MeOH/ CH2C12 (Rf. 0.5); 1H-NMR (DMSO-i/tf, 400 MHz): delta 10.66 (s, 1H), 10.61 (s, 1H), 7.24 (d, J= 6.4 Hz, 1H), 7.18 (s, 1H), 6.85 (d, J = 8.4 Hz, 1H).

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ARNOLD, Lee Daniel; MAAG, Hans; TURNER, JR., William W.; (274 pag.)WO2016/168619; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 615-16-7, The chemical industry reduces the impact on the environment during synthesis 615-16-7, name is 2-Hydroxybenzimidazole, I believe this compound will play a more active role in future production and life.

Step 1: (0389) 1H-benzimidazol-2(3H)-one 19-a (500 mg, 3.73 mmol) was added into anhydrous aluminum chloride (1.98 g, 14.9 mmol) and tetrachloroethane (3 ml). Chloroacetyl chloride (843 mg, 7.46 mmol) dissolved in tetrachloroethane (3 ml) was added dropwise thereto under ice bath followed by stirring at 100 C. for 1 hour. The mixture was cooled to room temperature, ice and 4N hydrochloric acid (20 ml) were added sequentially followed by stirring for 6 hours, the precipitated solid was filtered, the filter cake was slurried in isopropanol, filtered, and dried to give 19-b as an off-white solid (730 mg, yield: 93%). EI-MS (m/z): 210.

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, 2-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); 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. 615-16-7, name is 2-Hydroxybenzimidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Hydroxybenzimidazole

An ice-cold mixture of sodium hydride (8.00 g, 60% dispersion in mineral oil, 200 mmol) and 145 (8.94g, 66.6 mmol) in DMF (250 mL) under a dry nitrogen atmosphere was allowed to gradually warm to room temperature. To the resulting mixture, iodoethane (16 ml, 200 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was taken up in hexanes and filtered. The resulting brown solid was dried under reduced pressure to give 146 (9.00 g, 71% yield). This material was used without purification. [0394] Step Two: A mixture of DMF (3.6 g, 49 mmol) and POCl3 (9.6 mL, 100 mmol) was stirred at room temperature under a dry nitrogen atmosphere for 1 hour. The flask containing this mixture was then placed in a 45 C. oil bath and 146 (7.6 g, 40 mmol) was added in small portions. The oil bath temperature was raised to 70 C. and the mixture was stirred overnight, then cooled to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a 7:3 mixture of 147:146 (6.69 g). This material was used without purification.

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; Biediger, Ronald J.; Chen, Qi; Decker, E. Radford; Holland, George W.; Kassir, Jamal M.; Li, Wen; Market, Robert V.; Scott, Ian L.; Wu, Chengde; Li, Jian; US2004/63955; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 615-16-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 615-16-7 name is 2-Hydroxybenzimidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: 4-Bromo-2-(substituted) benzonitrile 5a or 5b (5 mmol) was added to a mixture of 1H-benzo[d]imidazol-2(3H)-one (6) (10 mmol) and Cs2CO3 (10 mmol) in DMF (25.0 ml). After 12 h, 50 ml of ice water was added dropwise. The resulting suspension was filtered, and the filter cake was dried in a vacuum oven. The solid was purified by flash chromatography (50 % ethyl acetate in hexane) to afford 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(substituted) benzonitrile (7a or 7b). 2-(Trifluoromethyl)-4-(1,2-dihydro-2-oxobenzo[d]imidazol-3-yl) benzonitrile (7a) Yield 62 %; White Solid; mp 232-233 C; IR (KBr) nu max: 3189, 3149 (N-Hstretch), 3072 (C-Harom), 2957, 2895, 2820 (C-Halk), 2230 (C:N), 1720 (C=O), 1611 (N-Hbend), 1575, 1507, 1481, 1439 (C=Carom), 1385, 1319, 1240, 1185, 1127, 1053 (C-Hbend), 1272, 558 (C-CF3) cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 9.372 (s, 1H, NH), 8.14 (s, 1H, H-2), 8.03 (d, 2H, H-5,H-6), 7.2 (m, 4H, phenyl); 13C NMR (100 MHz, CDCl3, ppm): delta 152.9 (C=O), 139.2 (C4), 135.6 (C6), 133.8, 133.1 (q, J = 65 Hz, C2), 128.5 (C0 1), 127.6 (d, J = 34 Hz, C5), 123.3 (C0 6), 122.8 (C0 3), 122.5 (q, CF3), 121.6 (C), 120.4 (C0 5), 114.8 (CN), 110.0 (C0 2), 108.7 (C0 4), 106.6 (C1); HRMS (ESI): m/z calculated for C15H8F3N3O [M?H]?: 304.06922; Found: 304.069.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Hydroxybenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Elancheran; Saravanan; Choudhury, Bhaswati; Divakar; Kabilan; Ramanathan; Das, Babulal; Devi; Kotoky, Jibon; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 539 – 552;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6N2O

sodium hydride (55% w/w dispersion in oil, 2.8 g) was added portionwise to a solution of 2,3-dihydrobenzimidazol-2-one (4.3 g) in DMF (100 ml) which had been cooled in an ice-water bath. The mixture was stirred at ambient temperature for 1.5 hours, during which period a further portion of DMF (50 ml) was added to aid the stirring of the reaction mixture. methyl iodide (5 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and with brine, dried (MgSO4 and evaporated. The residue was purified by column chromatography using a 2:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained 1,3-dimethyl-2,3-dihydrobenzimidazol-2-one (3.14 g, 60%), m.p. 104-106C.

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENECA LIMITED; ZENECA Pharma S.A.; EP462831; (1996); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 615-16-7, 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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under N2 protection, 2(3H)-benzimidazolone 2 (20 g, 149 mmol) was dissolved in CH2Cl2 (75 mL). The solution was cooled to 5 oC and AlCl3 (48 g, 358 mmol) was carefully added as a solid in three equal portions over 10 min. Then ,2-chloropropionyl chloride 3 (21 g, 169 mmol) was added dropwise. After the addition, the reaction mixture was warmed up and stirred for 17 h at room temperature. Then, AlCl3 (10 g, 75 mmol) was added and the reaction mixture was stirred for 2 h at 25 oC. The reaction mixture was slowly poured into acooled mixture (pre-cooled to 5 oC) of heptane (300 mL) and H2O (300 mL). The result mixture was stirred for 15 h at 25 oC. Filtration of the mixture gave a wet cake, which was washed by H2O (200 mL), followed by heptane (100 mL). The resulting cake was dried over 50 oC for 3 h to give compound 4 (33 g,98%); a brown solid; mp 142-144 oC; IR (KBr, max cm-1): 3197, 3095, 2987, 2857, 1750, 1674, 1473,1276, 1201, 872, 708 cm-1; 1H-NMR (400 MHz, DMSO-d6): = 1.60 (d, J = 4.8 Hz, 3H), 5.75 (q, J = 4.8Hz, 1H), 7.06 (d, J = 6.3 Hz, 1H), 7.55 (s, 1H), 7.66 (d, J = 6.3 Hz, 1H), 10.98 (br s, 1H), 11.16 (br s, 1H)ppm; 13C-NMR (100 MHz, DMSO-d6): = 20.62, 53.66, 108.63, 109.14, 123.86, 127.02, 130.37, 135.23,155.90, 193.11 ppm; HRMS (ESI): calcd. for C10H10ClN2O2 225.0431 [M+H]+; found 225.0431. Anal.Calcd for C10H9ClN2O2: C, 53.47; H, 4.04; Cl, 15.78; N, 12.47. Found: C, 53.40; H, 3.95; Cl, 15.71; N,12.38.

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, 2-Hydroxybenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zou, Ping; Hu, Lin; Yan, Xi-Meng; Li, Xiao-Yue; Wei, Wanguo; Qiu, Xiao-Long; Gou, Shao-Hua; Heterocycles; vol. 98; 5; (2019); p. 674 – 680;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 615-16-7, name is 2-Hydroxybenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 615-16-7

Sodium hydride (55% w/w dispersion in oil, 2.8 g) was added portionwise to a solution of 2,3-dihydrobenzimidazol-2-one (4.3 g) in DMF (100 ml) which had been cooled in an ice-water bath. The mixture was stirred at ambient temperature for 1.5 hours, during which period a further portion of DMF (50 ml) was added to aid the stirring of the reaction mixture. Methyl iodide (5 ml) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water and with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 2:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained 1,3-dimethyl-2,3-dihydrobenzimidazol-2-one (3.14 g, 60%), m.p. 104-106 C.

The synthetic route of 615-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5179115; (1993); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem