Author: Jessica.F

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. 15469-97-3, name is 1-Trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 15469-97-3

A cooled (-78°C) yellow solution of 1-(triphenylmethyl)imidazole (25.000 g; 80.542 mmol) in anhydrous THF (750 ml) was treated dropwise (in 55 min.) with a 1.6M solution of butyllithium in hexanes (55.35 ml; 88.560 mmol). After addition, the resulting pink homogeneous solution was further stirred at -78°C, under nitrogen, for 30 min. before a solution of anhydrous DMF (6.8 ml; 88.186 mmol) in anhydrous THF (40 ml) was added dropwise (in 40 min.). The resulting mixture was additionally stirred at -78°C, under nitrogen, for 1 h before aq. sat. NH4CI (50 ml) was added dropwise. Ether (300 ml) and water (400 ml) were successively added, and this mixture was allowed to warm-up to rt. The yellow organic layer was additionally washed with water (300 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM / MeOH = 30 / 1 ) to give the pure product 1 -trityl-1 H-imidazole-2- carbaldehyde as a pale yellow solid which was further dried under HV (20.660 g; 76percent). LC-MS: tR = 1.03 min.; [M+H]+: no ionisation.

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; ACTELION PHARMACEUTICALS LTD; WO2008/78291; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, 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 3012-80-4, HPLC of Formula: C9H8N2O

General procedure: Benzimidazole 1 or 2 (1 mmol)was added to the mixture of TfOH (1 mL) or H2SO4 (2 mL) and arene (2-18 mmol). Reactionmixture was stirred at room temperature for the time as indicated in Table 3 or Scheme 2. Themixture was poured into ice water (30 mL). After extraction with CH2Cl2 (3 × 30 mL), thecombined extracts were consequently washed with water (50 mL), saturated aqueous solution ofNa2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporated in vacuo to givecrude products, which was subjected to chromatographic separation on silica gel using petroleumether/diethyl ether as an eluent.

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:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
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

Electric Literature of 89830-98-8, A common heterocyclic compound, 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, molecular formula is C6H8N2, 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: A mixture of 9-(2-methyloxazol- 4-yl)-3,4,7,8-tetrahydro-[1 ,4]diazepino[7,1-a]isoquinoline-2,5-dione (140 mg, 0.45 mmol) in DCE (10 mL) was treated with POCI3 (84 mu, 0.91 mmol) and heated to 100 °C for 1 h. The mixture was then allowed to cool to RT, poured onto cold H20 and extracted with DCM. The org. phases were dried over Na2SO,, filtered and concentrated in vacuo. The brown residue obtained was taken up in DCE (5 mL) and 4-cyclopropyl-1H-imidazole (59 mg, 0.54 mmol) and pyridine (110 mu, 1.36 mmol) were then added. The mixture was heated to 100 DC for 1 h, and then allowed to cool to RT, poured onto H20 and extracted with DCM. The org. layers were then dried over Na2S04. filtered and concentrated in vacuo. Purification by SFC (column: 2-Ethylpyridine 5 muetaiota, 250 x 30 mm, 60A, Princeton; eluent: 10percent MeOH/C02 for 1 min, then from 10percent MeOH/C02 to 15percent MeOH/C02 in 6 min; then from 15percent MeOH/C02 to 50percent MeOH/C02 in 1 min; flow 100 mL/min; UV detection at 220 nm) afforded the title compound (42 mg) as beige powder. UPLC-MS: MS 400.2 (M+H+); UPLC rt 0.86 min. 1H NMR (400 MHz, CHLOROFORM- : delta ppm 0.61 – 0.82 (m, 2 H); 0.82 – 0.91 (mr 2 H); 1.78 – 1.96 (m, 1 H); 2.56 (s, 3 H); 3.16 (t, J=6.02 Hz, 2 H); 3.89 (t, J=6.15 Hz, 2 H); 4.37 (br. s., 2 H); 6.62 (s, 1 H); 7.19 (d, J=1.25 Hz, 1 H); 7.38 – 7.48 (m, 1 H); 7.63 – 7.70 (m, 2 H); 7.78 (dd, J=7.65, .13 Hz, 1 H); 7.89 (d, J=1.26 Hz, 1 H).

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; NOVARTIS AG; BEHNKE, Dirk; CARCACHE, David; ERTL, Peter; KOLLER, Manuel; ORAIN, David; WO2014/30128; (2014); A1;,
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

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

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

Synthetic Route of 496-46-8, 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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

tetraallylglycoluril A three-neck 100 ml flask was flushed with argon. Anhydrous DMSO (40 ml) was added and glycoluril (1.42 g, 10 mmol) was dissolved. Then potassium tert-butoxide (5.62 g, 50 mmol) was gradually added and the mixture was further stirred for 1.0 h. Allyl bromide (7.0 ml, 80 mmol) was injected into the reaction mixture and the reaction was performed at 25C for 20 h. 500 ml aqueous solution of HCl (0.1 M) was added into the reaction mixture. 100 ml ethyl acetate was used to extract the mixture andthe organic phase was washed by saturated NaCl aqueous solution(100 ml) for three times. After being dried by MgSO4, the solventwas removed. 1.53 g target product was obtained after purifica-tion over silica column with the eluent of ethyl acetate/petroleumether (60-90C) (v/v, 3:2). All procedures were performed in argonatmosphere.

The synthetic route of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Bingfeng; Li, Fengbo; Huang, Zhijun; Lu, Tao; Yuan, Guoqing; Applied Catalysis A: General; vol. 481; (2014); p. 54 – 63;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 144689-93-0, name is Ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 144689-93-0

Example 3; Preparation of olmesartan medoxomilTo dimethyl acetamide (800 ml) was added 4-(1-hydroxy-1-methylethyl)-2-propyl imidazol- 5-carboxylic acid ethyl ester (100 gms) and powdered potassium carbonate (200 gms). To this was charged 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide (300 gms) at 45-50C. The contents were stirred for 8-10 hours at 45-50C. The insolubles were filtered. The contents were cooled to 5-100C. Potassium tertiary butoxide (100 gms) was charged at a temperature below 45C. The reaction was maintained at 40-450C for 3 hrs. To this was slowly added 5-methyl-2-oxo-1 ,3-dioxane-4-yl) methyl chloride at 40-450C over a period of 1 hour. The contents were heated to 60-650C and maintained for 4 hours. The reaction mass was then cooled to 30-350C and was neutralized with concentrated hydrochloride acid. The reaction mass was filtered to remove inorganics. The reaction mass was charcoalized using charcoal (10 gms) and was stirred for 30 minutes at 40-450C. The reaction mass was filtered over hyflo. The clear filtrate was acidified with hydrochloric acid (100 ml) slowly at 25-30C. The contents were stirred at 60C for 1 hour. The reaction mass was chilled to 0-5C and was filtered to remove tritanol. The reaction mass was concentrated under reduced pressure. The residue was quenched with water (500 ml), neutralized with base and extracted in dichloromethane (500 ml).The clear dichloromethane extract was then concentrated under reduced pressure, stripped off with acetone. The residue thus obtained was isolated from the acetone (250 ml) to give 55 gms of the title compound. Chromatogrphic purity- > 99%

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; CIPLA LIMITED; CURTIS, Philip, Anthony; WO2008/43996; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem