Tag: M.W=200-300

Synthetic Route of 144689-93-0, A common heterocyclic compound, 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, molecular formula is C12H20N2O3, 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.

Into a 100-mL two-neck flask were sequentially added imidazole 4(5 g, 21.0 mmol), bromide 3 (9.05 g, 22.3 mmol), K2CO3 (5.1 g,37.4 mmol) and MeCN (50 mL) at 25 C. The reaction mixture washeated at 84 C until completion of the reaction (18 h). Then, themixture was cooled to 25 C and filtered through Celite. TheCelite bed was washed with EtOAc (2 × 10 mL). To the combinedEtOAc layer was added H2O (100 mL). The resulting two layerswere separated and the aqueous layer was extracted with EtOAc (3× 50 mL). The combined organic layer was washed with 2% aq HCl(30 mL) followed by brine (150 mL). The organic layer was driedover Na2SO4 and concentrated under reduced pressure to give 1a;yield: 9.78 g (83%)

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:
Article; Seki, Masahiko; Synthesis; vol. 46; 23; (2014); p. 3249 – 3255;,
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. 37148-86-0, name is 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 37148-86-0

Reference Example 2 (0.12 g)2-bromo-4-nitroaniline (0.12 g), cesium carbonate (0.28 g), copper (I) oxide (8.1 mg) and 4,7- dimethoxy-1,10 -Phenanthroline (0.027 mg) was added. The reaction solution was stirred under microwave irradiation at 180 C. for 1 hour and then cooled to room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (elution solvent; hexane: ethyl acetate) to obtain Example 40 (30 mg).

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; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; ISOBE, YOSHIAKI; BAN, HITOSHI; SAITO, YASUHIRO; WATANABE, HITOSHI; (44 pag.)JP2018/135270; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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 compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) containing piperidine (0.50 mL) ethyl orthoformate (1.48 g, 0.01 mol) and aniline oil (0.93 g, 0.01 mol) was added. The reaction mixture was heated under reflux for 3 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Pale yellow crystals from ethanol; yield: 2.35 g (79%); m.p. >300 oC. IR, : 3471-3329 (NH), 3055 (CH aromatic), 2980, 2873 (CH3, CH2), 1699 (CO), 1643 (C=N), 1629 (C=C). 1H-NMR: : 1.15 (t, 3H, J = 7.13 Hz, CH3), 4.23 (q, 2H, J = 7.13 Hz, CH2), 6.03 (s, 1H, CH=C), 7.26-7.42 (m, 9H, C6H5, C6H4), 8.23, 8.34 (2s, 2H, 2NH, D2O exchangeable). 13C NMR (DMSO): 16.2 (ester CH3), 52.5 (ester CH2), 88.4, 90.3 (C=C), 120.6, 121.6, 123.6, 123.8, 124.1, 125.3, 126.4, 127.3, 128.8, 129.5 (C6H5, C6H4), 164.8 (CO), 173.3 (C=N), Anal. calcd for C18H17N3O2: C, 70.34; H, 5.58; N, 13.67%. Found: C, 70.29; H, 5.73; N, 13.82%. MS: m/z: (%) 307 (M+, 22%).

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohareb, Rafat M.; Gamaan, Marwa S.; Bulletin of the Chemical Society of Ethiopia; vol. 32; 3; (2018); p. 541 – 557;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, 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: 144689-93-0

An eggplant flask was charged with 5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester (10 g, 41.7 mmol; imidazole derivative (compound of formula (4b)), 4-bromobenzyl bromide (10.8 g, 43 mmol; dihalogen compound),Dimethylacetamide (40 ml; first reaction solvent (DMA)) was added to a mixture of potassium carbonate (7.1 g, 51.6 mmol; base) and stirred for 48 hours. After the reaction, water (120 mL) was added to the reaction solution and stirred. The precipitated crystals were filtered and recrystallized from ethyl acetate to give 3- (4-bromobenzyl) -5- (1-hydroxy-1-methylethyl) -2-propyl-3H-imidazole-4-carboxylic acid ethyl ester(A halogenated imidazole derivative (compound of the formula (1b))) 8 g (yield 47%).

The synthetic route of 144689-93-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokuyama Corporation; Sekine, Masahiko; Tanaka, Kenji; (31 pag.)JP2018/154611; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33529-02-1, 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 33529-02-1 as follows.

In einem Autoklaven wurden 0,25 Mol 1-Decylimidazol, welches durch die Radziszewski-Reaktion aus Glyoxal, Formaldehyd, Ammoniak und 1-Decylamin zugaenglich ist (siehe Ullmann’s Encyclopedia of Industrial Chemistry, 6th edition, 2000 electronic release, Chapter “IMIDAZOLE AND DERIVATIVES – Production), und 0,3 Mol Dimethylcarbonat in 100 ml Methanol zusammen mit 1,5 g Kaliumcarbonat und 0,1 g 18-Krone-6 12 Stunden auf 135C erhitzt. Nach dem Abkuehlen wurde der Reaktionsaustrag filtriert und mit 150 ml 50%iger waessriger Tetrafluoroborsaeure (Fa. Acros) versetzt. Nun wurde fuer eine Stunde unter Ruehren auf 50C erwaermt und anschliebetaend die waessrige Phase abgetrennt. Die verbleibende organische Phase wurde erneut mit 100 ml 50 %iger waessriger Tetrafluoroborsaeure versetzt, fuer eine weitere Stunde unter Ruehren auf 50C erwaermt und die waessrige Phase abgetrennt. Der organische Rueckstand wurde nun zweimal mit Cyclohexan extrahiert und danach im Vakuum bei 80C von Loesungsmittelresten befreit. Es wurden 0,16 Mol 1-Decyl-3-methylimidazolium-tetrafluoroborat erhalten, was einer Ausbeute von 64 % entspricht.

According to the analysis of related databases, 33529-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; EP1398318; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 14741-71-0, A common heterocyclic compound, 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate, molecular formula is C11H12N2O2, 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.

A solution of compound (4a-b) (4 g, 0.022 mol) in absoluteethanol (15 mL) was refluxed for 7 h in presence of conc. H2SO4(0.1 mL). After completion of the reaction, it was cooled to roomtemperature, then 2.14 ml (0.044 mol) of hydrazine hydrate wasadded and the reaction was further refluxed for another 8 h.Detecting single-spot in TLC using the solvent system chloroform:methanol (9:1), the reaction mixture was poured in ice. A precipitateformed (6a-b) which was filtered, washed with water andcrystallized from ethanol. 4.4.1. 2-(1H-benzo[d]imidazol-2-yl)acetohydrazide (6a, C9H10N4O)white flakyYield 86%, mp 120-122 C; Rf 0.40 [chloroform: methanol(9:1)]; IR (KBr) (cm1): 3360 (NH str), 1733 (C]O); 1H NMR(300 MHz, DMSO-d6) delta(ppm): 3.66 (s, 2H, NH2), 4.28 (s, 2H, CH2C] O), 7.11e7.12 (d, 2H, J 3.6, H-5,6 benzimidazole), 7.47 (s, 2H, H-4,7benzimidazole), 9.36 (s, 1H, eNHNH2), 12.22 (bs, 1H, NH benzimidazole,D2O exchangeable). 13C NMR (75 MHz, DMSO-d6) delta(ppm): 164.38, 149.56, 137.68, 133.50, 125.50, 121.27, 45.06. Anal.Calcd.: C, 56.83; H, 5.30; N, 29.46; Found: C, 56.85; H, 5.34; N, 29.43.

The synthetic route of 14741-71-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Akhtar, Md Jawaid; Siddiqui, Anees Ahmad; Khan, Ahsan Ahmed; Ali, Zulphikar; Dewangan, Rikeshwer Prasad; Pasha, Santosh; Yar, M. Shahar; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 853 – 869;,
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. 1450-93-7, name is 1H-imidazol-2-amine sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows., name: 1H-imidazol-2-amine sulfate(2:1)

2-Aminoimidazole sulfate (1.53 g) is dissolved in 0.97 mL of concentrated HCl, 1 mL of water, and 3 mL of acetic acid. The resulting solution is cooled to 0 C. A solution of 799 mg of NaNO2 in 2 mL of water is added dropwise, and 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 1.65 g of 1,4-diallyl-1,2,3,4-tetrahydroquinoxaline, 1.9 g of sodium acetate and 10 mL of acetic acid is cooled to 0 C. The diazonium solution is added slowly to this slurry 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 the dark solid is dried. (E)-6-((1H-imidazol-2-yl)diazenyl)-1,4-diallyl-1,2,3,4-tetrahydroquinoxaline (2.3 g) is used in the next step without further purification.

According to the analysis of related databases, 1450-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Procter & Gamble Company; MURPHY, Bryan Patrick; ZHANG, Guiru; ZHAO, Jielu; (32 pag.)US2018/72970; (2018); 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. 86604-86-6, name is 2-Chloro-6-(trifluoromethyl)benzimidazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClF3N2

Example 1 8-(5-(Trifluoromethyl)-1H-benzo[d]imidazol-2-yloxy)quinolin-2-ol A mixture of 2-chloro-5-(trifluoromethyl)-1H-benzo[d]imidazole (66 mg, 0.3 mol, prepared according to the procedure described in WO 2004/035549 A1), 2,8-dihydroquinoline (48 mg, 0.3 mmol, Fluka) and N,N-diisopropylethylamine (0.1 mL, 0.58 mmol, Aldrich) in EtOH (2 mL) was subjected to microwave irradiation at 180 C. with stirring for 60 min. The reaction mixture was allowed to cool to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluding with 80% EtOAc/hexane to give the title compound as an amorphous solid. MS (ESI, pos. ion) m/z: 346 (M+1).

According to the analysis of related databases, 86604-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Norman, Mark H.; Ognyanov, Vassil I.; Wang, Xianghong; US2006/160872; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-87-0, name is 4-Iodo-1-methyl-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 71759-87-0, Formula: C4H5IN2

Preparation 78tert-butyl (3S,4R)-4-{[3-carbamoyl-5-( 1-methyl-i H-imidazol-4-yl) pyridin-2-ylloxy}-3-fluoropiperidine- 1 -carboxylate To a solution of tert-butyl (3S,4R)-4-{[3-carbamoyl-5-(4,4, 5, 5-tetramethyl- 1, 3,2-dioxaborolan-2- yl) pyridin-2-yl]oxy}-3-fluoropiperidine- 1 -carboxylate (Preparation 99, 900 mg, 1.94 mmol) and 4- iodo-i-methyl-1H-imidazole (403 mg, 1.94 mmol) in DMF (15 mL) was added a solution of potassium carbonate (534 mg, 3.87 mmol) in water (2 mL) and the mixture degassed with argon for 15 minutes. i,i-bis(diphenylphosphino)ferrocene palladium (II) dichloride (79 mg, 0.097mmol) was added and the reaction heated to 100C for 16 hours. The reaction was cooled, diluted with EtOAc, washed with water, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 3-5% MeOH in DCM to afford the title compound (400 mg, 49%).1H NMR (400 MHz, DMSO-d6): O ppm 1.41 (5, 9H), 1.81-1.86 (m, 1H), 1.96-1.99 (m, 1H), 2.95-3.30 (m, 2H), 3.68 (5, 3H), 3.98-4.03 (m, 1H), 4.10-4.21 (m, 1H), 5.00 (d, 1H), 5.42-5.50 (m, 1H),7.53 ( br 5, 1 H), 7.67 (5, 1 H), 7.69 (5, 1 H), 7.82 (br 5, 1 H), 8.54 (d, 1 H), 8.63 (d, 1 H). MS mlz 420 [M+H]

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; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); 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, Application In Synthesis of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole

36.0 g (174 mmol) 6H-benzimidazolo[1 ,2-a]benzimidazole, 77.8 (174 mmol) 3-iodo-9-(p- tolylsulfonyl) carbazole, 106 g (0.500 mol) potassium phosphate, 5.5 g (28.9 mmol) copper iodide, and 11 1 g (0.972 mol) trans-cyclohexane-1.2-diamimne in 900 ml dioxane are stir- red at 100 C for 48 h under nitrogen. The product is filtered off, washed with dioxane and ethanol and is used without purification for the next reaction step.

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; BASF SE; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; MURER, Peter; HEINEMEYER, Ute; KOHLSTEDT, Julia; WOLLEB, Heinz; WOLLEB, Annemarie; WATANABE, Soichi; NAGASHIMA, Hideaki; SAKAI, Toshio; LENNARTZ, Christian; WAGENBLAST, Gerhard; WO2015/14791; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem