Tag: M.W=200-300

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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1) belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1H-imidazol-2-amine sulfate(2:1)

2-Aminoimidazole sulfate (659 mg) is dissolved in 0.42 mL of concentrated HC1, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 oC. To the solution is added 345 mg of NaN02 in 1 mL of water dropwise so the internal temperature is maintained below 5 C. The resulting yellow-brown solution is stirred for 30 minutes at 0 C. In a separate flask equipped with a mechanical stirrer a mixture of 1.0 g of 2,2,2-trifluoro-l-(4- pentyl-3,4- dihydroquinoxalin-l(2H)-yl)ethan-l-one, 0.82 g of sodium acetate and 3 mL of acetic acid is cooled to 0 C. To this slurry is added the diazonium solution slowly while stirring. After the addition is complete, the resulting red suspension is stirred for 1 hour at 0 C. The dark reaction mixture is poured into a beaker containing 10 g of ice. Aqueous NaOH (20%) is added to the suspension slowly until pH 6.5 is reached. The mixture is filtered and brick red solid is collected. The crude (E)-l-(7-((lH-imidazol-2-yl)diazenyl)-4-pentyl-3,4- dihydroquinoxalin-1 (2H)-yl)-2,2,2-trifluoroethan-l -one is dried and used in the next step without further purification (0.94 g).

The synthetic route of 1450-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOXELL CORPORATION; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (106 pag.)WO2018/53034; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 39861-21-7, 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. 39861-21-7, name is 4-(5-Chloro-1H-benzo[d]imidazol-2-yl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Further, compounds 4 (0.35-0.50 mmol, 1.0 eq) were heated withchloroacetyl chloride (3.0 eq) in anhydrous toluene (10 mL) to 90 C for2 h. This reaction mixture was concentrated under reduced pressureand the residue was triturated with diethyl ether (10 mL). The productwas filtered and subsequently washed with multiple portions of diethylether (3×5 mL) and dried to recover colored solids. The solids werevigorously stirred in a saturated solution of NaHCO3 (10 mL) for30 min, acidified to neutral pH by aqueous 1M HCl solution and thenextracted with multiple portions of ethyl acetate (5×10 mL) until theaqueous layer turns colorless. The combined organic extracts werewashed with brine (10 mL), dried over sodium sulfate (10 g), were filteredand concentrated to yield pure amides 5 as colored solids in70-90% yield.

The chemical industry reduces the impact on the environment during synthesis 4-(5-Chloro-1H-benzo[d]imidazol-2-yl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ankenbruck, Nicholas; Kumbhare, Rohan; Naro, Yuta; Thomas, Meryl; Gardner, Laura; Emanuelson, Cole; Deiters, Alexander; Bioorganic and Medicinal Chemistry; vol. 27; 16; (2019); p. 3735 – 3743;,
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Imidazole | C3H4N2 – PubChem

Electric Literature of 870837-18-6, 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. 870837-18-6 name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, 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.

Synthesis of (Z)-(6S*,9aR*)-6-(4-fluorophenyl)-3-[1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]hexahydropyrido[2,1-c][1,4]oxazin-4-one Triethylamine (0.03 mL) was added to a solution of [(6R*,9aS*)-6-(4-fluorophenyl)-4-oxooctahydropyrido[2,1-c][1,4]oxazin-3-yl]triphenylphosphonium bromide (57 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (21 mg) in ethanol (5 mL), and the reaction solution was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 27 mg of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 1.40-1.58(m,2H), 1.65-1.76(m,2H), 2.18-2.25(m,2H), 2.31(s,3H), 3.85(s,3H), 4.07(q,J=10.8 Hz,1H), 4.07-4.15(m,1H), 4.34(dd,J=10.8,2.4 Hz,1H), 5.38(t,J=4.0 Hz,1H), 6.82(s,1H), 6.92(brs,1H), 7.02(t, J=8.4 Hz,2H), 7.20(d,J=8.0 Hz,1H), 7.22(dd,J=8.0,3.6 Hz,2H), 7.37(dd,J=8.0,1.2 Hz,1H), 7.39(d,J=1.2 Hz,1H), 7.74(d,J=1.2 Hz,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/117798; (2007); 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 641571-13-3 as follows. Computed Properties of C12H9F3N2O2

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid (10 mg, 0.030 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (22 mg, 0.058 mmol), and TEA (7.9 mg, 0.078 mmol) were dissolved in DMF (0.2 ml), the solution was stirred at 45 C. for 30 minutes, and then the compound F (10 mg, 0.030 mmol) was added, followed by stirring the solution at 45 C. for 12 hours. After the reaction was completed, ethyl acetate was added, and the reaction mixture was washed with a saturated aqueous NaCl solution. The organic layer was dried with sodium sulfate anhydrous and filtered, and then the solvent was removed under reduced pressure. The residue was crystallized to obtain a target compound 3-(4-methyl-1H-imidazol-1-yl)-N-(4-(2-oxo-2,3-dihydro-1H-thieno[3,4-b][1,4]diazepine-4-yl)phenyl)-5-(trifluoromethyl)benzamide (10.3 mg, 67%). 1H NMR (400 MHz, DMSO-d6) delta 10.77 (1H, s), 10.53 (1H, s), 8.49 (1H, s), 8.43 (1H, s), 8.27 (1H, s), 8.19 (1H, s), 8.09 (2H, d, J=8.8 Hz), 7.95 (2H, d, J=8.8 Hz), 7.75 (1H, s), 7.52 (1H, d, J=4.0 Hz), 7.02 (1H, d, J=3.6 Hz), 3.61 (2H, s), 2.19 (3H, s) (Exact mass 509.11, m/z 510.1193)

According to the analysis of related databases, 641571-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Industry-University Cooperation Foundation Hanyang University ERICA Campus; HAH, Jung-Mi; LEE, Jung Hun; KIM, Minjung; (30 pag.)US2018/37589; (2018); 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. 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7BrN2O2

250 mg (1.14 mmol) of the bromide (ABCR), 400 mg (1.14 mmol) of 2-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphanyl]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 39 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) were initially charged in a mixture of degassed acetonitrile (4 ml) and degassed sodium carbonate solution (1M, 5 ml), and the mixture was stirred at 72 C. for 14 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure, and the residue was taken up in dichloromethane. The organic phase was washed with water, dried over magnesium sulphate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography purification using a cyclohexane/acetone gradient as mobile phase. (0569) log P (acidic/neutral): 3.09/3.19; MH+: 363; 1H-NMR (400 MHz, D6-DMSO) delta ppm: 2.46 (s, 3H), 3.71 (s, 3H), 3.83 (s, 3H), 3.99 (q, 2H), 7.42 (d, 1H), 7.75 (d, 1H), 7.81 (s, 1H).

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; Bayer CropScience Aktiengesellschaft; JANSEN, Johannes-Rudolf; HEIL, Markus; FISCHER, Reiner; WILCKE, David; WILLOT, Matthieu; ILG, Kerstin; EILMUS, Sascha; LOeSEL, Peter; ANDERSCH, Wolfram; (69 pag.)US2019/47982; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 152628-03-0, name is 4-Methyl-2-propyl-1H-benzo[d]imidazole-6-carboxylic acid, 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 152628-03-0, category: imidazoles-derivatives

4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 – 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 – 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 – 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 – 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 – 8.5 with aqueous ammonia solution. EPO Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 – 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 – 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 – 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 – 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 – 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 – 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4%). Water content by KF is 5.85%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MATRIX LABORATORIES LIMITED; WO2007/10558; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113775-47-6, name is Dexmedetomidine, 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 113775-47-6, name: Dexmedetomidine

A mixture of (+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1H-imidazole (dexmeditomidine; 2.00 g, 10.0 mmol) prepared as described in Cordi et al., Synth. Comm. 26: 1585 (1996), in THF (45 mL) and water (40 mL) was treated with NaHCO3 (8.4 g, 100 mmol) and phenylchlorothionoformate (3.7 mL, 27.4 mmol). After stirring for four hours at room temperature, the mixture was diluted with water (30 mL) and ether (75 mL). The organic layer was removed, and the aqueous layer extracted twice with a 50 ml volume of ether. The organic layers were dried over MgSO4 and filtered. The residue was concentrated under vacuum, diluted with MeOH (54 mL) and reacted with NEt3 (6.5 mL) at room temperature for 16 hours. The solvent was removed under vacuum and replaced with 30% CH2C12:hexane. The solvent was removed again and solids formed. After further resuspension in 30% CH2C12:hexane, the solid was collected on a filter, washed with CH2C12:hexane and dried under vacuum to give Compound 1 ((+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1,3-dihydro-imidazole-2-thione) 1.23 g (53%). A schematic of the preparation of Compound 1 is shown above. Characterization of the product yielded the following. Optical rotation: [a]D20+14 (c 1.25 in MeOH). 1H NMR: (300 MHz, DMSO) d 11.8 (s, 1H), 11.6 (s, 1H), 7.03-7.01 (m, 2H), 6.95-6.91 (m, 1H), 6.50 (s, 1H), 4.15 (q, J=6.9 Hz, 1H), 2.25 (s, 3H), 2.20 (s, 3H), 1.38 (d, J=6.9 Hz, 3H).

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

Reference:
Patent; Allergan, Inc.; US2005/59721; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 24155-42-8, A common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, molecular formula is C11H10Cl2N2O, 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.

EXAMPLE 4 2-(4-Chlorophenyl)-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]thiazole, hydrochloride (1:1) Following the procedure of Example 1b, 4-chloromethyl-2-(4-chlorophenyl)thiazole (m.p. 66) is reacted with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol to yield the title compound, m.p. 108-110 C. (acetonitrile).

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4307105; (1981); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2963-77-1, 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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Using a typical scale of 1.0 mmol, 1 (1.0 mmol) was dissolved inanhydrous pyridine (2 mL) in a small round-bottomed flask and themixture was cooled to 40 C after which the acid chloride(2.0 mmol; purchased or prepared as above) in dry THF or DMF(2 mL) was added dropwise over 20 min with vigorous stirring.After 2-6 h the reaction mixturewaswarmed to room temperatureand the solvent reduced under pressure. Without using a work-upthe crude product was purified by column chromatography directlyusing MeOH/DCM mixtures (1:99 to 2:8).

The synthetic route of 4-(1H-Benzo[d]imidazol-2-yl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; L’abbate, Fabrizio P.; Mueller, Ronel; Openshaw, Roxanne; Combrinck, Jill M.; de Villiers, Katherine A.; Hunter, Roger; Egan, Timothy J.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 243 – 254;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, 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 14741-71-0, Recommanded Product: Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate

4-Amino-3-(1H-benzimidazol-2-yl)-5-(4-ethylpiperazin-1-yl)quinolin-2(1H)-one t-BuLi (3.1 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) and 6-amino-2-(4-ethylpiperazinyl)benzenecarbonitrile (1.0 eq) in THF at 0 C. The reaction was stirred overnight. The resulting mixture was quenched with NH4Cl (aq, saturated) and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was triturated with CH2Cl2 and MeOH to provide a tan solid. LC/MS m/z 389.1 (MH+), Rt 1.80 minutes.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Renhowe, Paul A.; Pecchi, Sabina; Machajewski, Timothy D.; Shafer, Cynthia M.; Taylor, Clarke; McCrea JR., William R.; McBride, Christopher; Jazan, Elisa; US2002/107392; (2002); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem