Category: imidazoles-derivatives

Reference of 14741-71-0, 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. 14741-71-0, name is Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 3 (2.04 g, 0.01 mol) in ethanol (40 mL) containing triethylamine (0.50 mL) phenylisothiocyanate (1.30 g, 0.01 mol) was added. The reaction mixture was heated under reflux for 4 h then poured onto ice/water mixture containing few drops of hydrochloric acid and the formed solid product was collected by filtration. Yellow crystals from ethanol; yield: 2.67 g (87%); m.p. 202 oC. IR, : 3057 (CH aromatic), 2980 (CH2), 1689 (CO), 1643 (C=N), 1632 (C=C).1H-NMR: : 5.90 (s, 2H, pyrimidine CH2), 7.26-7.38 (m, 9H, C6H4, C6H5). 13C NMR (DMSO): 54.2 (CH2), 120.3, 123.7, 124.1, 124.6, 124.9, 125.8, 129.3, 126.7, 127.2, 128.2 (C6H5, C6H4), 163.4 (CO), 173.6 (C=N), 180.3 (C=S); Anal. calcd for C16H11N3OS: C, 65.51; H, 3.78; N, 14.32; S, 10.93%. Found: C, 65.33; H, 4.02; N, 14.59; S, 11.27%. MS: m/z: (%) 293 (M+, 22%).

The synthetic route of Ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate 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;,
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Related Products of 3012-80-4, 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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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.

The synthetic route of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde has been constantly updated, and we look forward to future research findings.

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;,
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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. 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H6N2S

STEP A 2-methylthio-1-methyl-imidazole 10 ml of a solution of 1.5% diazomethane in methylene chloride were added in 3 portions over 15 minutes at 0 C. to a solution of 1.14 g of 2-mercapto-1-methyl-imidazole in 5 ml of methylene chloride and after stirring at 0 C. for one hour, a second addition of 10 ml of the diazomethane in methylene chloride solution was made. The mixture was stirred at 20 C. for one hour and was then evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 1-1 methylene chloride-ethyl acetate mixture to obtain 1 g of 2-methylthio-1-methyl-imidazole.

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 60-56-0.

Reference:
Patent; Roussel Uclaf; US5663164; (1997); A;,
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Reference of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 t-BuOK (1 M in THF, 0.80ml) was added dropwise to a stirred mixture of B6 (R7 = p-SF5-Phenyl and R6 = carboethoxyl, 0.41 g) and A1(157 mg, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol-1 -yl) and R8 = H) in 10 ml_ of anhydrous THF at -70eC under nitrogen atmosphere. The reaction mixture was stirred between -709C and -30QC until starting material were consumed. The reaction was quenched with iced brine, and extracted with EtOAc. The organic phase was washed with aqueous NH4CI and brine, dried over anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was purified by a flash silica gel column and eluted with DCM/MeOH to give 0.38g B7 (R7 = p-SF5-Phenyl, R6 = carboethoxyl, R10 = 3-MeO-Phenyl, R9 = 4-(4-Methyl-imidazol- 1-yl)).

The synthetic route of 870837-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; XU, Ruo; CLADER, John, W.; WO2010/54064; (2010); A1;,
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Electric Literature of 870837-18-6,Some common heterocyclic compound, 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, molecular formula is C12H12N2O2, 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 tetrahydrofuran (20 mL) solution containing (1S,6R,9aR)-6-(4-chlorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione (685 mg) was cooled to -30 C. L-selectride (3.01 mL, 1.02 M tetrahydrofuran solution) was added dropwise, and stirring was continued for 2 hours at -20 C. to -30 C. 5 N sodium hydroxide solution (460 muL) was added to the reaction solution, and stirring was continued for 20 minutes at -20 C. to 0 C. Next, hydrogen peroxide solution (221 muL, 35% solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (237 mg) was added, and after stirring at room temperature for 20 minutes, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (19.4 mL) and triphenylphosphonium bromide (796 mg) was added to the residue, and the resultant was heated under reflux for 2 hours. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (543 mg) and triethylamine (633 muL) were added, and stirring was continued for 12 hours at room temperature. The solvent was removed under a vacuum, and ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under vacuum, and the residue was purified by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate), and the title compound (640 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 480 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.48 (d, J=6.4 Hz, 3H), 2.29 (s, 3H), 3.51 (dd, J=11.2, 11.2 Hz, 1H), 3.74 (dd, J=12.0, 8.0 Hz, 1H), 3.83 (s, 3H), 3.99 (dd, J=11.2, 4.0 Hz, 1H), 4.18 (dd, J=12.4, 4.8 Hz, 1H), 4.41 (ddd, J=11.6, 4.0, 4.0 Hz, 1H), 4.50-4.56 (m, 1H), 4, 86 (dd, J=8.0, 4.4 Hz, 1H), 7.82 (s, 1H), 6.91 (s, 1H), 7.18 (d, J=8.8 Hz, 1H), 7.32-7.35 (m, 6H), 7.69 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, its application will become more common.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
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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 10040-98-9 as follows. category: imidazoles-derivatives

General procedure: A methanolic sodium hydroxide solution (10%; 10.0 mL) was added drop-wise to a mixture of 1-(4-(1H-imidazol-1-yl)phenyl)ethanone(3) (10.0 mmol, 1.86 g), aromatic aldehyde (10.0 mmol) and methanol (50 mL) over a period of 30-40 min with continuous stirring at room temperature until completion of the reaction (as indicated by TLC). The reaction flask was kept in the freezer overnight. The obtained precipitates were filtered off and washed with a cold methanol-water mixture (1:10). Finally the product was purified by column chromatography using CHCl3:MeOH (97:3) as a solvent.

According to the analysis of related databases, 10040-98-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hussain, Tanvir; Zia-Ur-Rehman, Muhammad; Zaheer, Muhammad; Ashraf, Chouhdary Muhammad; Bolte, Michael; Journal of Chemical Research; vol. 40; 4; (2016); p. 199 – 204;,
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Related Products of 71759-88-1,Some common heterocyclic compound, 71759-88-1, name is 5-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

Example 64 3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-5-(1-methyl-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine A solution of 5-iodo-1-methyl-1H-imidazole (0.0217 g, 0.104 mmol), 3-[(S)-1-(2-chloro-3-fluoro-6-methoxy-phenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.030 g, 0.070 mmol), potassium carbonate (0.0289 g, 0.209 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (2.84 mg, 0.00348 mmol) in previously degassed 4:1 dioxane:water (1.50 mL) was evacuated and charged with N2 (2*) and heated under microwave conditions [Biotage, 100 C., 30 min, high absorption]. The reaction mixture was partitioned between EtOAc and H2O and separated. The aqueous was back extracted with EtOAc (3*) and the combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo resulting in a crude brown oil. The crude was purified by chromatography on silica gel [ISCO Combiflash, 12 g cartridge, eluting with 100% DCM-8% MeOH in DCM]. This resulted in the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): delta=1.82 (d, J=7.3 Hz, 3H), 3.51 (s, 3H), 3.66 (br. s., 3H), 5.12 (q, J=7.1 Hz, 1H), 6.90 (dd, J=4.2, 9.0 Hz, 1H), 6.95 (s, 1H), 7.08 (dd, J=8.8, 8.8 Hz, 1H), 7.41 (d, J=1.0 Hz, 1H), 7.51 (s, 1H), 7.69 (s, 1H), 8.17 (d, J=2.0 Hz, 1H). MS (ES+): m/z 385.11, 387.07 (76/24) [MH+]. HPLC: tR=2.87 min (polar-5 min, ZQ3).

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

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); 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 26663-77-4 as follows. Application In Synthesis of Methyl benzimidazole-5-carboxylate

To a solution of methyl 1H-benzo[d]imidazole-5-carboxylate (0.90 g, 5.1 mmol) in DMF(20 ml) was added NaH (0.25 g, 6.2 mmol), and the reaction mixture was stirred at room temperature for 30 mm. Then (2-(chloromethoxy)ethyl)trimethylsilane (0.94 g, 5.6 mmol) wasadded and the reaction mixture was stirred at room temperature for 2 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (100 mL), washed with H20 (100 mL x 2) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with petroleum ether/EtOAc = 1:1) to afford mixture ofmethyl 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazole-5-carboxylate and methyl 1- ((2-(trimethylsilyl)ethoxy) methyl)- 1 H-benzo [d] imidazole-6-carboxylate as an oil. LC/MS (m/z): 307 (M+H).To a solution of LiA1H4 (0.30 g, 7.8 mmol) in THF (20 ml) was added solution of Step A product (1.2 g, 3.9 mmol) in THF (30 mL) at 0C, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. When TLC showed that the reaction completed, the reaction mixture was quenched with sat. aq. NH4C1 (50 mL) and the mixture was filteredthrough a pad of celite. The filtrate was extracted with EtOAc (100 mL), washed with H20 (100 mL) and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford mixture of (1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo [d] imidazol-5-yl) methanol and (1- ((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl)methanol as an oil, which was used in next step without further purification. ?H NMR (CDC13, 400 MHz) oe 8.03 (s, 1H), 8.02(s, 1H), 7.86-7.79 (m, 2H), 7.64 (s, 1H), 7.61-7.55 (m, 1H), 7.43 (d, J= 7.3 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 5.59 (s, 4H), 4.90 (s, 2H), 4.87 (s, 2H), 3.59-3.53 (m, 4H), 0.99-0.91 (m, 4H), 0.00 (s, 9H).To a solution of Step B product (0.3 g, 1.1 mmol) in DCM(10 ml) was added SOC12 (0.8 ml, 10.8 mmol) dropwise at 0C, then the reaction mixture was stirred at room temperature for 3 hours. When TLC showed that the reaction completed, the reaction mixture was diluted with DCM (50 mL), washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure to afford a mixture of 5-(chloromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d] imidazole and 6-(chloromethyl)- 1 -((2- (trimethylsilyl) ethoxy)methyl)-1H-benzo[d]imidazole as an oil, which was used in next step without further purification. LC/MS (m/z): 297 (M+H).To a solution of Intermediate 2 (0.20 g, 0.65 mmol), Step C product (0.29 g, 0.97 mmol) in acetone (4 ml) and DMF (2 ml) was added K2C03(0.27 g, 1.9 mmol). The reaction mixture was then heated to 60 C and stirred for 6 hours. When LCMS showed that the reaction completed, the reaction mixture was diluted with EtOAc (1 OOmL), washed with H20 (100 mL)and brine (100 mL), dried over Na2504 and concentrated under reduced pressure to afford crude product as an oil, which was purified by column chromatography on silica gel (eluted with Petroleum ether/EtOAc = 1:1) to afford a mixture of tert-butyl 2-(4-hydroxy-2-oxo-1-((1-((2- (trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-5 -yl)methyl)- 1,2,5 ,7-tetrahydrofuro [3,4- b]pyridine -3 -carboxamido)acetate and tert-butyl 2-(4-hydroxy-2-oxo- 1 -((1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-benzo[d]imidazol-6-yl) methyl)- 1,2,5,7- tetrahydrofuro [3,4- b]pyridine-3-carboxamido)acetate as a solid. LC/MS (m/z): 571 (M+H).

According to the analysis of related databases, 26663-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DU, Xiaoxing; DUBOIS, Byron Gabriel; LIU, Ping; LIU, Rongqiang; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (61 pag.)WO2016/49100; (2016); A1;,
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Synthetic Route of 934-32-7,Some common heterocyclic compound, 934-32-7, name is 1H-Benzo[d]imidazol-2-amine, molecular formula is C7H7N3, 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: In a round-bottom flask, catalyst 1 {[HIMI]C(NO2)3}(1.0 mol%, 2.2 mg) was added to a mixture of the corresponding aromatic aldehyde (1.0 mmol), 2-aminobenzimidazole(1.0 mmol, 133 mg), and malononitrile (1.0 mmol,66 mg). The obtained mixture was stirred magnetically at50 C under solvent-free conditions for the appropriate time. After completion of the reaction, as identified by TLC(n-hexane/EtOAc: 5/3), EtOAc (10 mL) was added, and the mixture was stirred and refluxed for 10 min. Then, the resulting solution was washed with water (10 mL). Separation of the phases led to the crude product in the EtOAc phase while catalyst 1 was soluble in water. The organic phase was dried (MgSO4) and the solvent evaporated to afford the corresponding crude product which was purified via recrystallization from ethanol/water (10:1).

The synthetic route of 934-32-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yarie, Meysam; Zolfigol, Mohammad Ali; Baghery, Saeed; Khoshnood, Abbas; Alonso, Diego A.; Kalhor, Mehdi; Bayat, Yadollah; Asgari, Asiye; Journal of the Iranian Chemical Society; vol. 15; 10; (2018); p. 2259 – 2270;,
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Synthetic Route of 152628-02-9,Some common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[d]imidazole, molecular formula is C19H20N4, 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 an appropriate benzimidazole (5.03mmol) and NaH (0.12g, 5.53mmol, 60%) in 100mL anhydrous THF was stirred for 30minat 50C. After cooling to rt, a mixture of an appropriate bromide (6.04mmol) in anhydrous THF (50mL) was added dropwise to the solution. The solution was stirred for 3hat 50C. Then the resulting mixture was poured into 30mL ice water, and extracted with ethyl acetate (50mL×3). The combined organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by CC to give the product as white solid 4.1.7.8 [5-[[2-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl](phenyl)methanone (15c) 15c was prepared by following the above general procedure. Yield: 85.6%. MP: 214-217 C. 1H NMR (400 MHz, CDCl3): delta 8.35 (d, 1H), 7.86 (s, 1H), 7.78 (d, 2H), 7.60 (t, 2H), 7.54 (t, 2H), 7.43 (s, 2H), 7.34 (d, 2H), 7.31 (t, 2H), 7.28 (d, 1H), 6.73 (d, 1H), 5.68 (s, 2H), 3.74 (s, 3H), 2.94 (t, 2H), 2.78 (s, 3H), 1.85 (m, 2H), 1.04 (t, 3H). MS (ESI): [M + H]+ calcd 538.3; found 538.3.

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
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