Category: imidazoles-derivatives

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., HPLC of Formula: C12H20N2O3

Weigh 24.0 g of compound 1, 55.7 g of compound 2, And add 124g of potassium carbonate, Then 200 mL of butanone was added, Warmed to 60 C, Stir for two hours, Cool to 45 , The composite catalyst (a mixture of polyethylene glycol 400 and N, N-dimethylacetamide in a mass ratio of 5: 1) Continue stirring for 4 hours, TLC detection, Show two kinds of raw materials are not left. The reaction is over, filter, The filtrate was collected, concentrate, Get oil, A mixture of 50 mL of ethanol and water (2: 1 by volume) Stirring, A large number of solid precipitation, filter, Collect the solid, Washed with 50mL n-hexane beating, The target compound 67.3g, Yield 93.8% The HPLC purity was 99.3%.

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; Disha Pharmaceutical Group Co., Ltd.; Zhang Zhaoxing; Zhang Hongqiang; Qin Litai; Li Wei; Li Zongwen; Xia Haijian; (6 pag.)CN103012382; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 4887-88-1, A common heterocyclic compound, 4887-88-1, name is 5-Bromo-1H-benzo[d]imidazole, molecular formula is C7H5BrN2, 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 crude, impure 5-bromobenzimidazole (46.2 g) and methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate (Synthesis, 1984, 10, 847-850) (42 g, 220 mmol) in 800 mL of CHCl3 was added N-methylimidazole (28 mL, 345 mmol). After 16 h, N-methylimidazole (17 mL, 220 mmol) and tert-butylchlorodimethylsilane (36 g, 240 mmol) was added. When TLC showed the reaction to be complete, the solution was diluted with water. The layers were separated. The organic phase was washed with water, dried over MgSO4 and concentrated onto celite. The crude mixture was purified by flash column chromatography (0-25% EtOAc:hexanes) in batches to separate the 2 regioisomers, giving 33.5 g of Intermediate 3 eluting first and 29.2 g of Intermediate 4 eluting second (58%). (Intermediate 3, 5-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.77 (s, 1H), 8.01 (d, J=1.6 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.56 (dd, J=8.8 and 1.6 Hz, 1H), 7.25 (s, 1H), 3.76 (s, 3H), 0.99 (s, 9H), 0.27 (s, 6H). (Intermediate 4, 6-Br) 1H NMR (400 MHz, d6-DMSO) delta 8.71 (s, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.50 (dd, J=8.8 and 2.0 Hz, 1H), 7.26 (s, 1H), 3.77 (s, 3H), 0.99 (s, 9H), 0.26 (s, 6H).

The synthetic route of 4887-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kuntz, Kevin Wayne; Emerson, Holly Kathleen; Cheung, Mui; Badiang, Jennifer Gabriel; US2009/326029; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 268a 1-Methyl-4-nitro-1H-imidazole 268a To a mixture of 4-nitro-1H-imidazole (2.0 g, 17.7 mmol) and K2CO3 (3.67 g, 26.5 mmol) in acetonitrile (20 mL) was added iodomethane (1.3 mL, 3.0 g, 21.2 mmol) dropwise while stirring at room temperature. The resulting mixture was stirred at 60C overnight. It was then evaporated under reduced pressure and the residue was diluted with water (20 mL). The mixture was extracted with dichloromethane (2 X 20 mL). The combined extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 268a as a yellow solid (1.8 g, 82%). MS-ESI: [M+H]+ 128.1. 1H NMR (500 MHz, DMSO-d6) delta 8.37 (s, 1H), 7.82 (s, 1H), 3.76 (s, 3H).

The synthetic route of 5-Nitro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5993-91-9, name is (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride, 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 5993-91-9, name: (1H-Benzo[d]imidazol-2-yl)methanamine dihydrochloride

Preparation 1 2-(Aminomethyl)benzimidazole; Add 2-(aminomethyl)bcnzimidazole, dihydrochloride, hydrate (18.50 g) to a solution of potassium hydroxide (9.50 g) in methanol (400 mL). Stir the resulting mixture at room temperature for 30 minutes, filter, and concentrate the filtrate in vacuo. Extract the residue with EtOAc (5 x 500 mL) and filter. Concentrate the filtrate in vacuo to give the title compound as a white solid (9.60 g).

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-Benzo[d]imidazol-2-yl)methanamine dihydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; EP1135374; (2006); B1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 13570-08-6, The chemical industry reduces the impact on the environment during synthesis 13570-08-6, name is 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, I believe this compound will play a more active role in future production and life.

Thionyl dichloride (0.7 ml, 9.65 mmol) was added dropwise to an ice-cooled (0C) suspension of 2-(1H-1,3- benzodiazol-2-yl)acetic acid (179) (0.7 g, 3.97 mmol) in MeOH (30 ml). The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was poured onto saturated NaHCQ (40 ml) and extracted with DCM (3 x 20 ml). The combined organic layers were washed with brine (30 ml), dried (NaS04), filtered and evaporated to give the title compound (0.65 g, 86%) as a cream solid. 1H-NMR(CDCI3, 500 MHz): d[ppm]= 10.10 (brs, 1H), 7.72 (brs, 1H), 7.46 (brs, 1H), 7.29-7.23 (m, 2H), 4.09 (s, 2H), 3.82 (s, 3H) HPLCMS (Method F): [m/z]: 191.2 [M+Hf

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, 2-(1H-Benzo[d]imidazol-2-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2735-62-8, These common heterocyclic compound, 2735-62-8, name is 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)acetonitrile, 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 mixture of 1-methyl-1H benzoimidazol-2-yl)-acetonitrile (4)(23 mg, 0.13 mmol) and 4-methoxy-2-vinyloxy-benzaldehyde (3)(24 mg, 0.13 mmol) in ethanol (4 mL) were treated with one drop ofpiperidine at RT. The solution was stirred for 1 h. No starting wasleft in TLC. The reaction mixture was evaporated. The obtainedcrude mass was purified by column chromatography on silica,product eluted with 10-15% ethyl acetate in hexane to afford 3-(4-methoxy-2-vinyloxy-phenyl)-2-(1-methyl-1H-benzoimidazol-2-yl)-acrylonitrile(VPBA) (20 mg, 44.8%) as yellow solid. 1HNMR(400 MHz, CDCl3): delta (ppm) = 8.39-8.35 (m, 2H), 7.78 (d, J = 7.8 Hz,1H), 7.38-7.30 (m, 3H), 6.75 (d, J = 8.8 Hz, 1H), 6.60-6.56 (m, 2H),4.87 (d, J = 13.64 Hz, 1H), 4.58 (d, J = 5.76 Hz, 1H), 3.99 (s, 3H), 3.87(s, 3H). 13C NMR (100 MHz, CDCl3): 164.03, 157.61, 148.34, 146.96,145.08, 142.46, 136.71, 129.98, 123.58, 122.97, 119.95, 117.32, 115.98,109.68, 108.89, 102.37, 98.23, 97.37, 55.77, 31.63. MS (ESI): m/z calc.for C20H17N3O2: 331.13; found: 332.14 [M + H]+.

The synthetic route of 2735-62-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manna, Srimanta; Karmakar, Parthasarathi; Maiti, Kalipada; Ali, Syed Samim; Mandal, Debasish; Mahapatra, Ajit Kumar; Journal of Photochemistry and Photobiology A: Chemistry; vol. 343; (2017); p. 7 – 16;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 57090-88-7, These common heterocyclic compound, 57090-88-7, name is 1H-Imidazole-4-carbonitrile, 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 solution of 4-cyano-1H-imidazole (1000 mg, 10.74 mmol), 4-iodo -2-(trifluoromethyl)pyridine (3800 mg,14 mmol), (1R,2R)-N1,N2-dimethyl cyclohexane -1,2-diamine (150 mg, 1.07 mmol), CuI (200 mg, 1.07 mmol) and Cs2CO3 (7000 mg, 21.5 mmol) in 20 mL anhydrous DMF was stirred at 100 oC for 2 hours. The reaction mixture was cooled to room temperature and poured into 200 mL water. The mixture was extracted with ethyl acetate (80 mL*3). The organic layer were combined, washed by brine, dried by Na2SO4 and evaporated. The crude product was purified by silica flash column to afford compound 2 as white solid(1.5 g, 59percent yield).

Statistics shows that 1H-Imidazole-4-carbonitrile is playing an increasingly important role. we look forward to future research findings about 57090-88-7.

Reference:
Article; Zheng, Qiangang; Chen, Ziqi; Wan, Huixin; Tang, Shuai; Ye, Yan; Xu, Yuan; Jiang, Lei; Ding, Jian; Geng, Meiyu; Huang, Min; Huang, Ying; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3808 – 3812;,
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. 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 4-Iodo-1-trityl-1H-imidazole

Example 80; (IS, 2R) and (1R, 2S)-2-(4-(2-(4-chlorophenyl)-2′-oxospiro[cyclopropane-l,3′- indoline] – 1 ‘-yl)- lH-imidazol- l-yl)acetic acid; Synthesis of (IS, 2R) and (1R, 2S)-2-(4-chlorophenyl)-l’-(l-trityl-lH-imidazol-4- yl)spiro[cyclopropane-l,3′-indolin]-2′-one4-Iodo-l-trityl-lH-imidazole (210 mg, 0.48 mmol) was added to a suspension of racemic (I S, 2R)-2-(4-chlorophenyl)spiro[cyclopropane-l,3′-indolin]-2′-one (107 mg, 0.4 mmol) in acetonitrile (2 mL) under a nitrogen atmosphere. A steady stream of nitrogen was bubbled through the suspension as it was heated to 40 C over 15 minutes. Potassium carbonate (1 10 mg, 0.8 mmol), copper (I) iodide (12 mg, 15 mol %), and N,N- dimethylethylenediamine (0.12 mmol, 30 mol %) were added and the reaction mixture was heated to 80 C and kept for 21 hours under nitrogen atmosphere. The mixture was cooled to room temperature, filtered and concentrated to give the title product. The residue was purified by flash column chromatography (gradient elution, 5-10% ethyl acetate in petroleum ether) to give racemic trans-2-(4-chlorophenyl)-l’-(lH-imidazol-4- trityl)spiro[cyclopropane-l,3′-indolin]-2′-one(157 mg, 68%). LC/MS m/e calcd. for C38H28C1N30: 577, observed (M+H)+: 578.2MS calcd. for C38H28C1N30 578, obsd. (ESf) [(M+H)+] 579.3.

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; F. HOFFMANN-LA ROCHE AG; CHEN, Li; HUANG, Mengwei; FENG, Lichun; HE, Yun; YUN, Hongying; WO2011/69298; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 104619-51-4, 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. 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 34: r4-(5-Amino- PI ,3,4] oxadiazol-2-yl)-pyridin-3-v?-(4-bromo-2-fluoro- phenvD-amine; To a solution of 3-(4-Brorno-2-fluoro-phenylamino)-isonicotinic acid hydrazide (200mg, 0.62mmol, 1eq) in DMSO (2ml_) C- (Di-imidazol-i-yl)-methyleneamine (198mg, 1.23mmol, 2eq) was added. The reaction mixture was stirred at RT under argon overnight. It was then poured into water and the solid that precipitated out was filtered and washed with methanol to afford the desired product (195 mg). LC/MS (Method A) [0.62min; 351(M+1>]

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, Di(1H-imidazol-1-yl)methanimine, other downstream synthetic routes, hurry up and to see.

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

Reference of 6154-30-9,Some common heterocyclic compound, 6154-30-9, name is 2,5-Dibromo-4-nitro-1H-imidazole, molecular formula is C3HBr2N3O2, 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 mixture consisting of 2, 5-dibromo-4- nitroimidazole (27.1 g, 100 mmol) and concentrated hydrochloric acid (434 ml) was stirred under heating (77C to 80C, 16 hours). The reaction mixture was left to cool, and then stirred under cooling on ice (5C to 10C, 2 hours). Thereafter, the precipitated crystals were collected by filtration and air-dried (50C, 5 hours). The yield of the dried product was 8.26 g. The filtrate was further extracted with ethyl acetate (300 ml) and then dried (MgSO4), followed by vacuum concentration and exsiccation. The yield of the exsiccated product was 9.63 g. Thus, 17.9 g (in total) of 2, 5-dichloro-4-nitroimidazole was obtained (yield: 98. 3%). IR (KBr) : 1566,1475, 1403,1366, 1332,1272, 1190, 1091,996, 834,679 cm-l. MS (70 eV) m/z (relative intensity): 183 (15, M+), 181 (25), 108 (28), 74 (42), 62 (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dibromo-4-nitro-1H-imidazole, its application will become more common.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; WO2005/77913; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem