Month: May 2021

Reference of 129378-52-5,Some common heterocyclic compound, 129378-52-5, name is 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, molecular formula is C11H23N3O2SSi, 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 26: 4(5)-Chloro-1 H-imidazoleHO. alphaTo a solution of 2-[(1 ,1-dimethylethyl)(dimethyl)silyl]-N,N-dimethyl-1 H-imidazole-1- sulfonamide (for preparation see US2005075366,15 g, 51.8 mmol) in dry THF (100 ml_), under nitrogen and at -7O0C, a 1.6M solution of butyllithium in hexane (34.0 ml_, 54.4 mmol) was slowly added. The temperature was allowed to reach -550C in 1 hour then cooled down to -780C and dimethylsulfamoyl chloride (8.33 ml_, 78 mmol) was slowly added and the mixture was stirred at -780C for 30min and at 2O0C for 2 hours. The solvents were removed by evaporation and the residue was stirred with 2M HCI solution (100ml) for 12 hour at room temperature. Complete deprotection of the nitrogen was achieved while partial TBDMS deprotection was observed. The aqueous acid solution was basified with KOH pellets and the aqueous phase was extracted with EtOAc. The organic phases were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was treated with a 1 M solution of TBAF in THF (51.8 ml_, 51.8 mmol) and heated to 6O0C for 2 hours. The volatiles were removed under vacuo and the residue was chromatographed to give the title compound (3.5 g, 34.1 mmol); UPLC/MS Rt=O.33 min; m/z (ES): 103 and 105 [M+H]+; 1H NMR (CDCI3): delta 7.00 (d, 1 H), 7.57 (d, 1 H), 11.54 (brs, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; GIANOTTI, Massimo; LESLIE, Colin Philip; STASI, Luigi Piero; WO2010/142652; (2010); 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. 6953-65-7, name is (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6953-65-7

Step 2: synthesis of 4-(5-chloro-2-(hydroxymethyl)-1H-benzo[djimidazol-1- yl)butanenitrile (intermediate 21b) and 4-(6-chloro-2-(hydroxymethyl)-1H- benzo [dj imidazol-1-yl)butanenitrile (intermediate 21c)A mixture of (5 -chloro- 1 H-benzo [d]imidazo l-2-yl)methano 1 21 a (500 mg, 2.738 mmoles, 1 eq.), 4-bromobutyronitrile (466 mg, 1.15 eq.), cesium carbonate (1.338 g,1.5 eq.) and potassium iodide (45 mg, 0.1 eq.) in acetonitrile (5 mL) was refluxed overnight. The mixture was then cooled and filtered. The filtrate was evaporated under vacuum and the residue was treated with ethyl acetate (30 ml) and brine (20 ml). The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated under vacuum. The residue was purified by column chromatography (eluent: CH2C12:methanol from 1:0 to 15:1) to yield 732mg (54%) of a mixture containing the two regio-isomers 21b and 21c in a 1/1 ratio. This mixture was further separated by SFC to provide the pure regio-isomer 21b.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6953-65-7.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; HU, Lili; DEMIN, Samuel Dominique; COOYMANS, Ludwig Paul; WO2014/60411; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 253453-91-7, 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. 253453-91-7 name is 2-Chloro-1-methyl-1H-imidazole, 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.

Step A: (3-Fluoro-phenyl)-(2-chloro-3-methyl-3H-imidazol-4-yl)-methanol. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel is added 2-chloro-1-methyl-1H-imidazole (1 equiv.) and THF (0.5 M). The reaction mixture is cooled to -78 C. and n-BuLi (2.5 M in hexanes, 1.05 equiv.) is added. The resulting mixture is stirred for 1 h and a solution of 3-fluorobenzaldehyde (1.05 eq) in THF (2.5 M) is then added dropwise. After the addition is complete, the cooling bath is removed and the reaction is allowed to warm to rt. The reaction mixture is quenched with satd. aq. NH4Cl, transferred to a separatory funnel, and extracted with EtOAc. The organic layer is washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents are evaporated under reduced pressure to yield the product. The material is purified by recrystallization or column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68468-39-3, 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. 68468-39-3, name is 5-Bromo-1H-benzo[d]imidazole-2(3H)-thione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 2,4-Dinitrochlorobenzene (1 mmol), 2-mercapto-5-substituted benzimidazoles (1 mmol) and Potassium hydroxide (1 mmol) were suspended in aqueous-EtOH (1:1). The reaction mixture was stirred vigorously for about 30 minutes and then refluxed on water bath for 2.5 h, at which point it cleared and TLC analysis indicated complete consumption of the reactants. The reaction mixture was diluted with 50 mL of water and cooled in ice, and the precipitate was collected by filtration. After being washed with cold water (2 x 25 mL), the precipitate was dried under vacuum to afford a pure product (3a-d).

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

Reference:
Article; Kankala, Shravankumar; Kankala, Ranjith Kumar; Gundepaka, Prasad; Thota, Niranjan; Nerella, Srinivas; Gangula, Mohan Rao; Guguloth, Hanmanthu; Kagga, Mukkanti; Vadde, Ravinder; Vasam, Chandra Sekhar; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1306 – 1309;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 83279-44-1, 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. 83279-44-1, name is 1H-Imidazol-1-amine hydrochloride belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(d) 0.48 g of 1-aminoimidazole hydrochloride are suspended in 30 ml of ethanol, whereupon 0.93 g of 4-hydroxy-3,5-di-tert.-butylbenzaldehyde is added. The suspension is stirred at room temperature for 3 hours, whereby there results a clear solution which is evaporated in a vacuum. The residue is taken up in 15 ml of water, neutralized (pH=7) with ice-cold saturated sodium bicarbonate solution and extracted rapidly three times with 30 ml of methylene chloride each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated in a vacuum. By sublimation of the residue (160/12 Torr), there is obtained 1-(4-hydroxy-3,5-di-tert.-butylbenzylideneamino)imidazole of m.p. 171-174.

The synthetic route of 1H-Imidazol-1-amine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4908363; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5098-11-3, name is 5-Amino-1H-imidazole-4-carbonitrile, 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 5098-11-3, Formula: C4H4N4

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

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, 5-Amino-1H-imidazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Penn State Research Foundation; EP1420021; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

15965-57-8, name is 2-Chloro-7-methyl-1H-benzo[d]imidazole, 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: 15965-57-8

Step B: (8-Methyl-3H-l ‘-azaspiro[benzo[4,5]imidazo[2, l-b]oxazole-2,3 ‘- bicyclo[2.2.2]octan]-l ‘-yl-8-ium)trihydroborate To 2-chloro-7-methyl-lH-benzo[d]imidazole (0.65 g, 3.9 mmol) from example 10, step A, in THF (35 mL) was added n-butyllithium (1.6 mL, 3.9 mmol) dropwise at – 78C. After 45 minutes, a solution of racemic (l’-azaspiro[oxirane-2,3′- bicyclo[2.2.2]octan]-l’-yl-4-ium)trihydroborate (0.66 g, 4.29 mmol) from the reference example, in THF (10 mL) was added dropwise at -78C. The cooling bath ws removed and the reaction mixture warmed to room temperature. After 15 minutes, the mixture was heated to 75C for 2 hours and then cooled to room temperature. The reaction was quenched with water and the product was extracted with ethyl acetate (100 mL). The organics were dried with MgS04, filtered and the solvent was removed to yield the crude product. The crude material was purified by chromatography (Biotage) to yield racemic (8-methyl-3H-l’-azaspiro[benzo[4,5]imidazo[2, l-b]oxazole-2,3′-bicyclo[2.2.2]octan]-r- yl-10-ium)trihydroborate (0.40 g, 1.4 mmol, 52%). The 5-methyl regioisomer product was not observed. MS (LC/MS) R.T. = 1.90; [M+1-BH3]+ = 270.07.

The synthetic route of 15965-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; COOK II, James H.; ZUSI, F. Christopher; HILL, Matthew D.; (87 pag.)WO2016/73407; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 931-36-2,Some common heterocyclic compound, 931-36-2, name is 2-Ethyl-5-methyl-1H-imidazole, 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.

General procedure: alpha,beta-unsaturated compound (4.8 mmol) was added dropwise to a well stirred mixture of N-heterocycle substrate (4.0 mmol) in [n-butyl urotropinium]OH (0.108 g, 0.25 mmol) and the reaction mixture was stirred for required time until completion of reaction (TLC). The product was then directly distilled out from the reaction mixture to provide pure Michael adducts (3a-3f and 4a-4f) in high yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Ethyl-5-methyl-1H-imidazole, its application will become more common.

Reference:
Article; Kumar, Sitanshu; Kaur, Amanpreet; Singh, Vasundhara; Synthetic Communications; vol. 49; 2; (2019); p. 193 – 201;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 65039-05-6, name is 1-Butyl-3-methylimidazolium iodide, molecular formula is C8H15IN2, 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. Quality Control of 1-Butyl-3-methylimidazolium iodide

To a Schlenk flask charged with 1-butyl-3-methylimidazolium iodide (128.0mg, 0.48mmol) and Ag2O (56.0mg, 0.24mmol) was added dry CH2Cl2 (10mL), the mixture was protected from light and stirred at room temperature for 20h, before the resulting yellow solution was cannula filtered and added to a red solution of [(HMB)Ru(mu2-eta1,3-exo-syn-CH2CHCHCHO)]2(BF4)2 (200mg, 0.24mmol) in dry acetone (10mL). A solid immediately precipitated and the red suspension was stirred at room temperature protected from light for 4h, followed by filtration through a celite bed and washed with dry NO2CH3. The amber coloured solution was concentrated in vacuo to 5mL followed by addition of 20mL of dry diethyl ether and stored at-10C for 18h. The amber solution was taken to dryness resulting in a brown oil, washed with 10mL of pentane, vacuum dried and extracted with 10mL of dry toluene. Pentane (50mL) was added to the yellow toluene solution resulting in a yellow suspension which was stored at-10C for 20h, following by separation of an amber oil by decantation characterised as [(HMB)Ru(BuImMe)(eta3-CH2CHCHCOOH)](BF4) in very low yield just enough for NMR experiments. 1H NMR (CDCl3, 500MHz, ppm): 6.96 (2×d, J=1.8Hz, 1H, 4,5-Im), 4.47 (dt, J=6.7, 0.7Hz, 1H, H3-heteropentadienyl), 4.11 (m, 3H, overlap CH2-N-Im and H2-heteropentadienyl), 3.84 (s, 3H, CH3-N-Im), 3.09 (ddd, J=7.2, 1.5, 0.8Hz, 1H, H1syn-heteropentadienyl), 2.17 (s, 18H, HMB), 1.87 (dt, J=10.8, 1.1Hz, 1H, H1anti-heteropentadienyl), 1.79 (q, J=7.5Hz, 2H, CH2-CH2-N-Im), 1.34 (q, J=7.6Hz, 2H, CH2-CH2-CH2-N-Im), 0.95 (t, J=7.4Hz, 3H, CH3-(CH2)3-N-Im). 13C{1H} NMR (acetone-d6, 75MHz, ppm): 182.0 (C-Ru), 122.0 and 120.9 (C4,C5-Im), 96.0 (HMB), 92.5 (C2-heteropentadienyl), 65.7 (C3-heteropentadienyl), 52.8 (C1-heteropentadienyl), 51.7 (CH2-N-Im), 38.8 (CH2-CH2-N-Im), 33.6 (CH3-N-Im), 19.8 (CH2-CH2-CH2-N-Im), 16.4 (CH3-HMB), 13.7 (CH3-(CH2)3-N-Im). ESI-TOF-MS(+) (m/z): Calcd for [C24H37N2O2Ru]+ 487.189302, found 487.189566; error-0.540454ppm, DBE 7.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65039-05-6, its application will become more common.

Reference:
Article; Olguin, Juan; Diaz-Fernandez, Monica; de la Cruz-Cruz, Jose Ignacio; Paz-Sandoval, M. Angeles; Journal of Organometallic Chemistry; vol. 824; (2016); p. 33 – 41;,
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. 6953-65-7, name is (6-Chloro-1H-benzo[d]imidazol-2-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

General procedure: Solution ofbenzimidazole (0.1 mmol) in TfOH (1 mL) and arene (0.1 mL) was magnetically stirred at 140 Cin glass high pressure tube for 2.5 h, then poured into water (50 mL). After extraction with CH2Cl2(3 × 30 mL), the combined extracts were consequently washed with water (50 mL), saturatedaqueous solution of Na2CO3 (30 mL), water (50 mL), dried with anhydrous Na2SO4 and evaporatedin vacuo to give crude products, which were subjected to chromatographic separation on silica gelusing petroleum ether/diethyl ether as an eluent.

According to the analysis of related databases, 6953-65-7, the application of this compound in the production field has become more and more popular.

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