Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, 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 7189-69-7, category: imidazoles-derivatives

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

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, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 20485-43-2,Some common heterocyclic compound, 20485-43-2, name is 1-Methyl-1H-imidazole-2-carboxylic acid, molecular formula is C5H6N2O2, 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.

Methyl 4- [ (TERT-BUTOXYCARBONYL) AMINO]-L-METHYLPYRROLE-2-CARBOXYLATE (0. 1108 g, 0.43 mmol) in 4 M HC1/ETOAC (4.26 ml) was stirred at room temperature for 30 min. The solvent was removed under reduced pressure and dried under vacuum for 1 hr. The residue was dissolved in DMF (4 ml) and ImCOOH (0.059 g, 0.52 mmol, 1. 2 equiv) was added followed by HOBt (0.079 g, 0.65 mmol, 1.5 equiv), TBTU (0.189 g, 0.65 mmol) and Et3N (0.328 ml, 2.6 mmol, 6 equiv) and the solution stirred for 1 hr. Solvent was removed and purified by flash chromatography (0-5 % MEOH/DCM).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2-carboxylic acid, its application will become more common.

Reference:
Patent; UNIVERSITY OF WESTERN SYDNEY; WO2005/33077; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, 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 28890-99-5, Recommanded Product: 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

2.5 g (15.9 mmol) 2,3,4-trifluorobenzonitrile, 10.9 g (52.5 mmol) 6H-benzimidazolo[1 ,2- a]benzimidazole and 27.0 g (0.127 mol) potassium phosphate tribasic in 50 ml NMP (N-Methyl- 2-pyrrolidon) are stirred at 1 15 C under nitrogen for 18 h. The reaction mixture is filtered hot and the organic phase is poured on water. The product is filtered of. Column chromatography on silica gel with chloroform gives 1 .3 g (1 1.4 %) of the product. 1H NMR (300 MHz, DMSO-D6): rotamers: delta 8.55-8.82 (m, 2H); 6.41 -8.07 (m, 24H) MS (APCI(pos), m/z): 719 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole, and friends who are interested can also refer to it.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; RAIMANN, Thomas; SCHAeFER, Thomas; SAITO, Masatoshi; WOLLEB, Heinz; BENEDITO, Flavio Luiz; NISHIMAE, Yuichi; NAKANO, Yuki; NAGASHIMA, Hideaki; (111 pag.)WO2016/157113; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 1003-21-0, 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.

General procedure: 73: 2-methoxy-4-(1 -methyl-1 – -imidazol-5-yl)aniline Method F A suspension of 5-bromo-1 -methyl-1 H-imidazole (228 mg, 1.42 mmol), 2- methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (423 mg, 1 .70 mmol), Pd(PPh3)4 (164 mg, 0.142 mmol) and CsF (645 mg, 4.25 mmol) in DME/MeOH (9/3 mL) was stirred at 150^ under microwave irradiation for 60 minutes. The reaction mixture was filtered and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with between 0-4% MeOH in EtOAc to afford the title compound (137 mg, 48%). 1 H NMR (500 MHz, CDCI3): delta 7.56 (s, 1 H), 7.02 (s, 1 H), 6.81 – 6.76 (m, 3H), 3.95 (s, broad, 2H), 3.88 (s, 3H), 3.64 (s, 3H). LCMS (ESI) Rt = 0.43 minutes MS m/z 204 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0¡ãC, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10percent MeOH / DCM) afforded the title compound (1.4 g, 38percent, 90percent purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 – 7.49 (m, 2H), 7.29 – 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-5-chloro-N-(pyrimidin-2-ylmethyl)-1 ,3-thiazole- 4-carboxamide dihydrochloride (196) (563 mg, 0.94 mmol), 1 H-benzimidazole-2-carbaldehyde (178 mg, 1.22 mmol), DIPEA (0.654 ml, 0.74 mmol) in MeOH (15 ml) at room temperature for 24 h, followed by addition of NaBH4 (53 mg, 1.41 mmol) gave the title compound (224 mg, 54percent) as a white solid after purification by basic prep-HPLC. 1 H-NMR (DMSO-d6, 500 MHz): d[ppm]= 12.20 (br s, 1 H), 8.80 – 8.74 (m, 3H), 7.50 (br s, 2H), 7.40 (t, J = 4.9 Hz, 1 H), 7.21 – 7.07 (m, 2H), 4.64 (d, J = 5.9 Hz, 2H), 3.98 (s, 2H), 3.13 (t, J = 6.3 Hz, 2H), 2.96 (t, J = 6.3 Hz, 2H), 2.76 (br s, 1 H) HPLCMS (Method G): [m/z]: 428.2 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazole-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 15469-97-3, 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. 15469-97-3, name is 1-Trityl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Synthesis of 2-chloroimidazole (2-cim) To a 300-mL, three-neck, round-bottom flask equipped with a magnetic stirrer and argon inlet, were added N-tritylimidazole (3.14 g, 0.01 mol) and anhydrous THF (140 mL). The stirrer was started, and the solution was cooled to -78 C. (acetone/dry ice). n-BuLi (2.5 M in hexanes, 8.0 mL, 0.02 mol) was added via syringe resulting in reddish solution. This solution was stirred for 60 min whereupon hexachloroethane (5.0 g, 0.021 mol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 1 additional hour and then quenched with saturated aqueous ammonium chloride (100 mL). The cooling bath was removed, and when the reaction flask reached room temperature the contents were transferred to a 500 mL separatory funnel, and extracted with ethyl acetate (50 mL*2). The organic layer was separated, washed with water and brine, and dried over anhydrous sodium sulfate. After filtration, the solvents were evaporated under reduced pressure resulting in a slightly yellow solid. The solid was refluxed with 5% acetic acid in methanol (75 mL) for 24 hours. Upon evaporation of the solvent, water was added to the residue. Extraction with hexanes effectively removed the triphenylmethane impurity. Evaporation of water in vacuo afforded off-white solid as pure 2-chloroimidazole (2-cim, 0.70 g, 69% overall yield from N-triylimidazole).

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, 1-Trityl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; US2011/282067; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 20034-00-8, These common heterocyclic compound, 20034-00-8, name is (5-Nitro-1H-benzo[d]imidazol-2-yl)methanol, 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.

3.40b 2-chloromethyl-5-nitro-1H-benzimidazole 20 mL (275 mmol) thionyl chloride are added slowly to a solution of 6.4 g (33.1 mmol) (5-nitro-1H-benzimidazol-2-yl)-methanol in 100 mL DCM at 10 C. The reaction is stirred for 1 h at RT and the solvent is eliminated i.vac. The residue is triturated with DCM, suction filtered, washed with DCM and ether and dried in the circulating air dryer at 35 C. Yield: 7.01 g (100% of theory). C8H6ClN3O3 (M=211.609).

Statistics shows that (5-Nitro-1H-benzo[d]imidazol-2-yl)methanol is playing an increasingly important role. we look forward to future research findings about 20034-00-8.

Reference:
Patent; Boehringer Ingelheim Pharma GmbH & Co. KG; US2004/209865; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 2034-22-2, name is 2,4,5-Tribromoimidazole, 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 2034-22-2, Application In Synthesis of 2,4,5-Tribromoimidazole

To a cooled (0 C) suspension of sodium hydride (0.9 g, 0.03 mole) in THF (50 mL) was added dropwise a solution of 2, 4, 5-tribromo imidazole (5 g, 0.016 mol) in THF (50 mL). After lh, a solution of trimethylsilylethoxymethyl chloride (SEMC1) (3 mL, 0.017 mol) in THF (30 mL) was added dropwise. The reaction mixture was quenched with saturated ammonium chloride solution and then the reaction was extracted with ethyl acetate [3 x 100 mL]. The organic layers were combined and washed with 10 % sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered and concentrated to yield 7.2 g of Intermediate 37A as pale, yellow oil which solidified on standing. The material was used in the next step without further purification. MS (ESI) m/z: 435 (M+2+H)+.

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, 2,4,5-Tribromoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James, R.; FANG, Tianan; DECICCO, Carl, P.; PINTO, Donald, J., P.; ROSSI, Karen, A.; HU, Zilun; JEON, Yoon; QUAN, Mimi, L.; SMALLHEER, Joanne, M.; WANG, Yufeng; YANG, Wu; WO2011/100401; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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 89830-98-8, Computed Properties of C6H8N2

A mixture of 3-bromo-5-(trifluoromethyl)aniline (0.48 g, 2.0 mmol), 4-cyclopropyl-lH- imidazole (0.26g, 2.4 mmol), K2CO3 (0.35g, 2.5 mmol), CuI (57 mg, 0.30 mmol), and 8- hydroxyquinoline (44 mg, 0.30 mmol) in dry DMSO (2 mL) in a microwave tube was cooled to -78deg;C, and degassed by vacuum and refilled with N2 for three times. The mixture was heated at1200C overnight. The mixture was cooled to 40-500C and 14percent aq. NH4OH was added. The mixture was stirred at 40-500C for 1 h. After cooling, the mixture was diluted with water, and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (5percent MeOH in CH2Cl2) to afford the crude product (0.41 g). LCMS: (M+H)+= 268.3.

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTECH SOLUTION LLC; CHEN, Yongsheng; WO2010/96395; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture consisting of 4-nitroimidazole (100 g, 884 mmol), sodium bicarbonate (164 g, 1.94 mol), and water (500 ml) was intensively stirred, and thereafter, bromine (106 ml, 2.07 mol) was added dropwise to the mixture at room temperature (23C to 25C) over 6 hours (wherein it intensively foamed during the dropping). The thus obtained mixture was further stirred under heating (50C to 55C, 4 hours). Thereafter, water (400 ml) and concentrated hydrochloric acid (80 ml) were added thereto under cooling on ice (10C or lower), and the obtained mixture was stirred for 1 hours. Crystals were collected by filtration. The obtained crystals were washed with water (on a filter paper, with 400 ml of water), dispersedly washed (with 800 ml of water, twice), and air-dried (50C, 16 hours). Yield: 213 g (Yield: 88. 9%), pale yellow crystal IR (KBr): 3074,1548, 1468, 1392, 1361,1345, 1310, 1259,1172, 1066,975, 830,667 cm~l.

The synthetic route of 5-Nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/77913; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem