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. 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., category: imidazoles-derivatives

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

Reference of 693-98-1, 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 693-98-1 as follows.

Step 3aIodine (18.5 g, 73.1 mmol) was dissolved in 90 mL of chloroform. 2-Methylimidazole (3.0 g, 36.5 mmol) in 90 mL of 2M NaOH solution was added slowly.The cloudy mixture cleared to two phases by 2.5 h.The layers were separated and acetic acid (10.5 mL, 183 mmol) was added to the organic layer to neutralize the reaction (to pH~5-6).A solid appeared which was filtered off and recrystallized from warm acetonitrile to afford 8.5 g (69percent) of 4,5-diiodo-2-methyl-1H-imidazole. (M+H)+=334.

According to the analysis of related databases, 693-98-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (2011); 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. 15469-97-3, name is 1-Trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 1-Trityl-1H-imidazole

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

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., Product Details of 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

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 496-46-8 as follows. name: Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

A suspension of 28.4 g (0.2 mol) of glycoluril 1 and 80 g of 40% formaldehyde solution was alkalized with a 20% NaOH solution to 9-10, after which the mixture was stirred at 50 C for 2 h. 70% of water was distilled off, and tetra-N-hydroxymethyl glycoluril was separated and washed with acetone. Yield of 2 26.2 g (50%), mp 136.5 C. IR spectrum(KBr), nu, cm-1: 1718.31 (=), 3337.39 (). 1H NMR spectrum (400 MHz, DMSO), delta, ppm: 5.47 s(2H, CH), 4.62-4.79 m (8H, CH2).

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sal?keeva; Bakibaev; Khasenova; Taishibekova, Ye. K.; Sugralina; Minaeva, Ye. V.; Sal?keeva; Russian Journal of Applied Chemistry; vol. 89; 1; (2016); p. 132 – 139; Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.); vol. 89; 1; (2016); p. 103 – 111,9;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 288-32-4, name is 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 288-32-4, name: 1H-Imidazole

General procedure: To a stirred solution of 500 mg of the appropriate bromide 12 or 13 in 25 mL anhydrous acetone, under N2 at room temperature, is added 1.5 eq. of the desired nitrogenous heterocycle followed by 1.5 eq. of K2CO3 and 0.05 eq. of KI. The reaction mixture is left to react overnight at reflux temperature. The resulting solution is diluted with 100 mL of water and extracted with 3 × 30 mL EtOAc. The organic fractions are combined, washed twice with 30 mL KOH 1 M, twice with brine, dried over MgSO4, filtered and concentrated. The residue is purified by silica gel circular chromatography (eluent: EtOAc/Hex or MeOH/CH2Cl2) to yield the pure heterocyclic compounds. 1-substituted-1H-1,2,3-triazoles and 2-substituted-2H-1,2,3-triazoles (17/18, 19/20) were obtained simultaneously. These isomers were separated by silica gel circular chromatography.

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

Reference:
Article; Doiron, Jeremie; Soultan, Al Haliffa; Richard, Ryan; Toure, Mamadou Mansour; Picot, Nadia; Richard, Remi; Cuperlovic-Culf, Miroslava; Robichaud, Gilles A.; Touaibia, Mohamed; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4010 – 4024;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

51605-32-4, 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. 51605-32-4 name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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.

Using a modified procedure of Sreedhar. (Reference: Sreedhar, B., Synthesis, 795 (2008)). To a suspension of ethyl 4-methyl-1H-imidazole-5-carboxylate (0.530 g, 3.44 mmol) and (3-chloro-2-fluorophenyl)boronic acid (0.500 g, 2.87 mmol) in MeOH (5.74 mL) was added cuprous oxide (0.041 g, 0.287 mmol). The resulting purple suspension was stirred vigorously under an atmosphere of air (drying tube used). After 20 h, thereaction mixture was filtered to remove the solids and the clear blue filtrate was concentrated to give a blue solid. The blue solid was suspended in DCM and filtered to remove the solids and the blue filtrate was concentrated to give a pale blue solid weighing 0.187 g. Purification by normal phase chromatography gave ethyl 1-(3-chloro-2- fluorophenyl)-4-methyl- 1H-imidazole-5-carboxylate (0.0187 g, 2percent) as a clear, colorlessresidue and ethyl 1 -(3 -chloro-2-fluorophenyl)-5 -methyl- 1H-imidazole-4-carboxylate (Intermediate 24A) (0.0079 g, 1percent) as a clear, colorless residue. MS(ESI) m/z: 283.1 (M+H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-methyl-1H-imidazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PABBISETTY, Kumar Balashanmuga; CORTE, James R.; DILGER, Andrew K.; EWING, William R.; ZHU, Yeheng; (178 pag.)WO2017/19819; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 3034-41-1, A common heterocyclic compound, 3034-41-1, name is 1-Methyl-4-nitroimidazole, molecular formula is C4H5N3O2, 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.

Intermediate 10; 2-Chloro-N-(l-methyl-lH-imidazol-4-v?-7-r(4-methylphenyl)sulfonyl1-7H-pyrrolor2.3- J1pyrimidin-4-aminel-Methyl-4-nitro-lH-imidazole (Intermediate 1, 50 mg, 0.39 mmol) was dissolved in ethanol (5 mL) and Pd/C (5 wt%, Degussa, 20.93 mg, 9.83 mumol) was added. The reaction mixture stirred under 1 atm of hydrogen at r.t. for 3 hours and was then filtered through diatomaceous earth (Celite brand) to give 1 -methyl- lH-imidazol-4-amine. 2,4-Dichloro-7-[(4- methylphenyl)sulfonyl]-7H-pyrrolo[2,3-Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); 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 104619-51-4 as follows. Formula: C7H7N5

Example 2: r4-(5-Amino-M ,3,41oxadiazol-2-yl)-pyridin-3-v?-(2-fluoro-4-iodo- phenvD-amine; To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isoniotacotiniotac acid hydrazide (1g, 2.68mmol) in DMSO (6mL) were added 1 ,1 -di-1 H-imidazol-1-yl-methyleneamine (864mg, 5.36mmol). The reaction mixture was stirred at RT for 18h. Quenching of the reaction by adding water (6OmL). A solid precipitated out. The solid was filtered, washed with water and cold methanol. Yield: white solid 1.Og. LC-MS (Method A) [4.66min; 398(M+1)].

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/123936; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2,Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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: Method B: In a20 mL microwave Biotage tube, a 1M Na2CO3 aqueous solution(5 mL) purged with argon were introduced into a mixture purged with argon of 4-iodo-1H-imidazole (1a) (0.194 g, 1.0 mmol), a boronicacid 2 (1.6 mmol) and Pd(PPh3)4 (0.80 g, 0.05 mmol) in DMF (15 mL). The mixture washeated under microwaveirradiation. When the reaction was complete, the mixture was cooled toroom temperature and concentrated under reduced pressure. The residue waspurified by flash chromatography on silica gel to provide compounds 3j and 3p-3u in yields ranging from 30 to 95%. Time and temperaturereactions were collected in Table 1.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vichier-Guerre, Sophie; Dugue, Laurence; Pochet, Sylvie; Tetrahedron Letters; vol. 55; 46; (2014); p. 6347 – 6350;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem