Tag: M.W=100-200

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. 1262035-61-9, name is 5-Bromo-1-cyclopropyl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 1262035-61-9

A microwave vial was charged with 5-bromo-1-cyclopropyl-1H-imidazole (40 mg, 0.21 mmol), 3-methoxy-1-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1H-pyrazole-4-carboxamide (75 mg, 0.21 mmol), cesium carbonate (137 mg, 0.42 mmol) and Pd(dppf) G3 (20 mg, 0.02 mmol). Dioxane (1.5 mL) and water (75 muL) were added. The vial was purged with N2, sealed and irradiated in a biotage microwave at 120 C for 1 h. After this time he volatiles were removed under reduced pressure and the resulting black residue was taken up in DMSO and subjected to prep-HPLC (using a Sunfire Prep C18 OBD, 5mum 30x50mm column and using 95% water/5% MeCN (initial conditions) to 50% water/50% MeCN over 20 minutes in 0.1% TFA as the mobile phase at a flow rate of 50 mL/min). The fractions containing product were combined, evaporated to dryness and the resulting residue was dissolved in DCM (20 mL) and washed with satd. NaHCO3 (10 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the title compound (28 mg, 40%) as a white solid. 1H NMR (400 MHz, CDCl3) d ppm 8.53 (s, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.79 (s, 1H), 7.57 (d, J=0.8 Hz, 1H), 7.46 – 7.41 (m, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.25 (td, J=1.4, 7.8 Hz, 1H), 7.11 (d, J=1.3 Hz, 1H), 4.09 (s, 3H), 3.78 (s, 3H), 3.42 (tt, J=3.7, 7.2 Hz, 1H), 1.06 – 0.98 (m, 2H), 0.90 – 0.82 (m, 2H). MS (ESI): 338.1 [M + H]+.v

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; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; XIN, Zhili; HIMMELBAUER, Martin; JONES, John, H.; (147 pag.)WO2020/36949; (2020); 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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Methyl-1H-imidazole-2(3H)-thione

General procedure: A mixture of tosylhydrazone 1 (1 mmol), thiol 2 (1.5 mmol, 1.5 equiv), K2CO3 (2.5 mmol, 2.5 equiv) in toluene (4.0 mL) was stirred at 100 C for 24h under Argon. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature. After adding CH2Cl2 (10 mL), the organic phase was washed with saturated NaHCO3, brine and dried with Na2SO4, and concentrated under reduced vacuum. The residue was then purified by flash chromatography on silica gel to afford product 3.

According to the analysis of related databases, 60-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia-Carrillo, Mario Alfredo; Guzman, Angel; Diaz, Eduardo; Tetrahedron Letters; vol. 58; 20; (2017); p. 1952 – 1956;,
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Synthetic Route of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

4-lodo-1tf-imidazole (2.8g, 14.6mmol) and trityl chloride (5.Og, 20.5mmol) were dissolved in lambda/,lambda/-dimethylacetamide (45mL). The solution was cooled to 0″C and triethylamine (4mL, 29.2mmol) added slowly. The reaction mixture was slowly warmed to room temperature. After 48 hours the solution was poured to water(15OmL). The solid was filtered, washed with water, hexane and dried to give a white solid (5.7g) with a yield of 90%. The product was pure enough for the next step reaction without further 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; S BIO PTE LTD; WO2009/93981; (2009); A1;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 20970-50-7, The chemical industry reduces the impact on the environment during synthesis 20970-50-7, name is 1-(1-Methyl-1H-imidazol-5-yl)ethanone, I believe this compound will play a more active role in future production and life.

General procedure: nder an argon atmosphere, 9a (436 mg, 1.65 mmol) was dissolved in dry THF (30 mL) and the mixture was cooled to -65 C in a dry ice acetone bath. A n-BuLi hexane solution (1.6 M: 2.28 mL, 3.63 mmol) was added with stirring and the mixture was stirred at the same temperature for 1.5 h. After stirring, a solution of 6 (183 mg, 1.5 mmol) in dry THF (3 mL) was added dropwise and the whole was stirred at the same temperature for 1.5 h. After dilution with saturated aqueous ammonium chloride solution, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethanol and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was chromatographed on silica gel (CHCl3/7% ammonia in MeOH = 19:1) and crystallized from CHCl3 and diethylether to give 3c (121 mg, 26%) as a colorless powder.

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-Methyl-1H-imidazol-5-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ruchelman, Alexander L.; Man, Hon-Wah; Chen, Roger; Liu, Wei; Lu, Ling; Cedzik, Dorota; Zhang, Ling; Leisten, Jim; Collette, Alice; Narla, Rama Krishna; Raymon, Heather K.; Muller, George W.; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6356 – 6374;,
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Imidazole | C3H4N2 – PubChem

Application of 615-15-6, A common heterocyclic compound, 615-15-6, name is 2-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: All reactions were performed on a 0.50mmol scale relative to azoles. The benzotriazole(1a) (0.50 mmol), toluene (2a) (1.50 mmol), I2 (0.050 mmol) and TBHP (2 eq) weretaken in a round bottom flask equipped with stirrer. The resulting mixture was stirred for8 h at 100 oC. After cooling to room temperature, to the reaction mixture was addedwater (2 mL), and extracted with ester (3×10 mL). The combined organic phases werewashed with brine (2×5 mL), dried over anhydrous MgSO4 and concentrated in vacuo.The residue was subjected to flash column chromatography with hexanes/EtOAc (10/1)as eluent to obtain the desired 3aa a light yellow solid( 90% yield). The identity andpurity of the products was confirmed by 1H and 13C NMR spectroscopic analysis.

The synthetic route of 615-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiang; Yu, Guiqin; Li, Jihui; Wang, Dong; Chen, Yongxin; Shi, Keqin; Chen, Baohua; Synlett; vol. 24; 12; (2013); p. 1588 – 1594;,
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Imidazole | C3H4N2 – PubChem

Application of 38993-84-9, 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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1 -Methyl- 1 H-imidazol-5-yl)methanol was converted to the corresponding alkyl chloride by reaction with thionyl chloride in DCM. N-[1 -(Fluoromethyl)cyclopropyl]-3- [(1 -methylpyrazol-4-yl)methyl]-2,4-dioxo-1 1H-quinazoline-6-sulfonamide (100 mg, 0.260 mmol), the alkyl chloride (37 mg, 0.286 mmol) and potassium carbonate (43 mg, 0.312 mmol) in DMF was conventionally heated to 70 °C for 4 h. Usual work-up afforded the desired product (37 mg, 0.074 mmol, 28percent) as an off-white powder.

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-Methyl-1H-imidazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; MCGONAGLE, Alison E.; JORDAN, Allan; WASZKOWYCZ, Bohdan; HUTTON, Colin; WADDELL, Ian; HITCHIN, James R.; SMITH, Kate Mary; HAMILTON, Niall M.; (497 pag.)WO2016/92326; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 21252-69-7, 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. 21252-69-7, name is 1-Octyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In einen 2 I Schlenkkolben werden 830,5 g (5 mol) 1-Octylimidazol vorgelegt und 630,5g (5 mol) Dimethylsulfat portionsweise zugegeben. Der Ansatz wird danach 15 Minuten nachgeruehrt. Der Kolbeninhalt wird danach in ein 5I Becherglas ueberfuehrt und zu einer Mischung von 548,0g (5 mol) Natriumtetrafluoroborat in 2 Liter Wasser gegeben. Sofort bildetsich das Produkt als zweite, fluessige Phase. . Nach einer Phasentrennung wird die waessrige Phase noch einmal mit 1 Liter CH2Cl2extrahiert, und das organische Extrakt von Methylenchlorid befreit. Beide Produktfraktionen werden vereinigt und ueber Nacht bei 60°C am HV getrocknet. Man erhaelt 1-Octyl-3-methylimidazoliumtetrafluoroborat in 94 percentiger Ausbeute. Zum qualitativen Nachweis auf Chloridreste, werden ca. 1 ml des Produktes mit ca. 5 ml Wasser versetzt und mit 2 Tropfen konzentrierter Salpetersaeure angesaeuert. Zu dieser Loesung werden dann ca. 3-4 Tropfen Silbernitrat gegeben um etwaig vorhandenes Chlorid als Silberchlorid auszufaellen. Das Ausbleiben eines Silberchlorid-Niederschlags spricht fuer die komplette Abwesenheit von Chloridresten. [26.1] 1H-NMR (300 MHz, CDCl3):delta=9.3 ppm (s,1H,Ha); delta=7.26 ppm (d,1H,Hc); delta=7.24 ppm (d,1H,Hd); delta=4.1 ppm (t,2H,He); delta=3.9 ppm (s,2H,Hb); delta=1.6 ppm (m,2H,Hf); delta=1.2 ppm (m,10H,Hg,h,i,j,k); delta=0.8 ppm (t,3H,HI).13C-NMR (75 MHz, CDCl3):delta=137 ppm (C1); delta=124-122 ppm (C3,C4); delta=48 ppm (C5); delta=35 ppm (C2); delta=29-24 ppm (C6-C10); delta=20 ppm (C11); delta=13 ppm (C12).19F-NMR (281 MHz, CDCl3):delta= -151,3 ppm (d, 1J(BF)= 22 Hz)

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

Reference:
Patent; Solvent Innovation GmbH; EP1182196; (2002); A1;,
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. 4887-80-3, name is 5-Methoxy-1H-benzo[d]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 4887-80-3

To a solution of NaH (972 mg, 40.5 mmol) in DMF (20 mL) was added 5- methoxy-lH-benzo[d] imidazole (2.0 g, 13.5 mmol) at 27C. After stirring for 5 minutes, Mel (2.3 g, 16.2 mmol) was added and the resulting mixture was stirred for 16 h. The mixture was then diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the crude product (1.2 g, 54.5%) as a grown solid. This crude was used in next step without further purification. LCMS (m/z): 163.1 (M+l).

The synthetic route of 4887-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; JIN, Lei; WO2014/100730; (2014); A1;,
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 22884-10-2 as follows. Application In Synthesis of 2-(1H-Imidazol-1-yl)acetic acid

General procedure: Compound 1 (1.0 equiv) and DMAP (0.1 equiv)were mixed in a 100 mL round-bottom flask and dissolved by DMF and DCM. Then EDCI·HCl (1.0 equiv) and compounds 2g-2i (1.0 equiv) were separately added, and the reaction mixture was subjected to heating at 60C for 3 h. After the completion of the reaction, the solvent DCM was removed under reduced pressure. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography using a mixture of petroleum ether and EtOAc (3:2) to get compounds 3q-3u. (E)-3-Hydroxy-5-(4-hydroxystyryl)phenyl-2-(1H-imidazol-1-yl)acetate (3q). C19H16N2O4, light yellow solid, yield 90%; mp 167.8-168.4C. 1H NMR (500 MHz, DMSO-d6, delta, ppm, J/Hz): 9.86 (1H, s, 4?-OH), 9.07 (1H, s, 3-OH), 7.77(1H, s, H-1??), 7.41-7.35 (2H, m, H-2?, 6?), 7.06 (1H, d, J = 7.5, H-3??), 7.02 (1H, d, J = 7.5, H-2??), 6.92 (1H, d, J = 15.2, H-alpha),6.82 (1H, d, J = 15.1, H-beta), 6.78-6.75 (2H, m, H-3?, 5?), 6.74 (1H, s, H-2), 6.68-6.66 (1H, m, H-6), 6.56 (1H, t, J = 2.0, H-4),5.33 (1H, s, H-8a), 5.03 (1H, s, H-8b). 13C NMR (125 MHz, DMSO-d6, delta, ppm): 165.30 (C-7), 159.82 (C-3), 158.16 (C-4?),152.19 (C-5), 140.68 (C-1), 138.87 (C-1??), 130.07 (C-2?, 6?), 128.70 (C-1?), 128.61 (C-3??), 128.33 (C-alpha), 126.89 (C-beta),120.90 (C-3??), 116.37 (C-3?, 5?), 114.22 (C-6), 107.85 (C-2), 104.86 (C-4), 46.07 (C-8). HR-ESI-MS m/z 337.1188 [M + H]+(calcd for C19H17N2O4, 337.1194).

According to the analysis of related databases, 22884-10-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang; Ren; Du; Jin; Li; Xie; Chemistry of Natural Compounds; vol. 54; 5; (2018); p. 864 – 868; Khim. Prir. Soedin.; 5; (2018); p. 735 – 738,4;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 50995-95-4,Some common heterocyclic compound, 50995-95-4, name is 2-Propylimidazole, molecular formula is C6H10N2, 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.

Add 2-propylimidazole (0.22 g, 2.04 mmol) to a 150 mL round bottom flask.After stirring potassium carbonate as a base (0.30 g, 2.20 mmol) and acetonitrile as a solvent at 50 C for 40 minutes,After cooling to room temperature, intermediate V (0.43 g, 1.70 mmol) was added and the mixture was warmed to 75 C and the mixture was traced to the end of the reaction.After further concentration, extraction, column chromatography separation, drying and the like, the intermediate VII-4 (0.45 g) is obtained, the yield is 72.6%;a white solid

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

Reference:
Patent; Southwest University; Zhou Chenghe; Man Nabaonei·lamohan·laao·yadafu; Wang Juan; (39 pag.)CN110305064; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem