Tag: M.W=100-200

Application of 23785-21-9, 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. 23785-21-9, name is Ethyl 1H-imidazole-4-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ste -2: (0913) Preparation of ethyl 1-amino-1H-imidazole-5-carboxylate: (0914) [00346] To stirred solution of ethyl 1H-imidazole-5-carboxylate (0.1 g, 0.71 mmol) in N,N-dimethylformamide (10 mL) cooled to -10 C, was added lithium bis(trimethylsilyl)amide (0.78 mL, 0.78 mmol) drop wise and the reaction mixture was stirred at -10 C for 15 min. Then (aminooxy)diphenylphosphine oxide (0.199 g, 0.85 mmol) was added at -10 C and the reaction mixture was stirred at room temperature for 6 h. The reaction mixture was quenched by slow addition of water until the precipitate formed was dissolved to become clear solution. Then it was extracted using ethyl acetate (2 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound ethyl 1- amino-1H-imidazole-5-carboxylate as off white solid (0.1 g, crude). Calculated (M+H): 156.07; Found (M+H): 156.1.

The synthetic route of Ethyl 1H-imidazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUC THERAPEUTICS; ANDERSON, David, R.; VOLKMANN, Robert, A.; MENNITE, Frank, S.; FANGER, Christopher; (390 pag.)WO2017/100591; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 221289-88-9, 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. 221289-88-9, name is 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3,4-diaminobenzonitrile (2.60 g, 18.2 mmol) and pyridine (2 mL, 25 mmol) in DMF (20 mL) was added a solution of bis(trichloromethyl)carbonate (2.12 g, 7.14 mmol) in tetrahydrofuran (20 mL) dropwise under ice-cooling. The mixture was stirred at room temperature for 18 h. Dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. To the residue was added ethyl acetate, and then the precipitate was collected by filtration to give 2-hydroxybenzimidazole-5-carbonitrile (896 mg, 29%) as a purple solid. A mixture of the above compound (894 mg, 5.62 mmol) and phosphorus oxychloride (12 mL) was refluxed for 3 h. The reaction mixture was added to ice, and extracted with ethyl acetate. The extract was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography with n-hexane/ethyl acetate (2:3, v/v) to give the title compound (322 mg, 32%) as a white powder. LC-MS (ESI) m/z 178.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carbonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yoshida, Tomohiro; Akahoshi, Fumihiko; Sakashita, Hiroshi; Sonda, Shuji; Takeuchi, Masahiro; Tanaka, Yoshihito; Nabeno, Mika; Kishida, Hiroyuki; Miyaguchi, Ikuko; Hayashi, Yoshiharu; Bioorganic and Medicinal Chemistry; vol. 20; 16; (2012); p. 5033 – 5041;,
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Application of 53439-88-6,Some common heterocyclic compound, 53439-88-6, name is 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, molecular formula is C9H11N3O, 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 aniline (19d-e) (13.0 mmol), ethyl chloroformate (2.5 mL, 26.0 mmol) and Et3N (3.6 mL, 26.0 mmol) in anhydrous THF (150 mL) was stirred at room temperature for 30 min. The solid was filtered off and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL) and the organic layer was washed with water (3 ¡Á 50mL). The organic phase was evaporated under reduced pressure to give 20d-e in quantitative yield (98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one, its application will become more common.

Reference:
Article; Conconi, Maria Teresa; Marzaro, Giovanni; Urbani, Luca; Zanusso, Ilenia; Di Liddo, Rosa; Castagliuolo, Ignazio; Brun, Paola; Tonus, Francesca; Ferrarese, Alessandro; Guiotto, Adriano; Chilin, Adriana; European Journal of Medicinal Chemistry; vol. 67; (2013); p. 373 – 383;,
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Imidazole | C3H4N2 – PubChem

Application of 54624-57-6, The chemical industry reduces the impact on the environment during synthesis 54624-57-6, name is 2-Bromobenzimidazole, I believe this compound will play a more active role in future production and life.

(1) In a 250 mL three-necked flask, nitrogen gas was introduced, and 0.02 mol of the raw material B1, 0.03 mol of the raw material E1, 0.04 mol of sodium hydride,0.004 mol of cuprous iodide and 0.01 mol of phenanthroline are dissolved in 100 ml of 1,3-dimethyl-2-imidazolidinone, and the reaction is stirred for 20-30 h.After the reaction, water was added and the mixture was extracted with dichloromethane.The mixture was washed with a mixture of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the eluent was 1:100.Purification by column chromatography gave Intermediate X1; HPLC purity: 99.7%, yield 78.5%.

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-Bromobenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Wang Fang; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (57 pag.)CN109956933; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 1615-14-1

To a solution of tert-butyl (5-(5-fluoro-1H-indazol-3-yl)-1,2,4-oxadiazol-3- yl)methy .carbamate (1.5 g, 4.50 mmol, 1 equiv.) in anhydrous toluene was added in order: l-(2-hydroxyethyl) imidazole (0.55 g, 4.95 mmol, 1.1 equiv.), 77-butyl phosphine (1.78 ml, 7.2 mmol, 1.6 equiv.) and TMAD (1.24 g, 7.2 mmol, 1.6 equiv.). The clear orange solution was allowed to stir under nitrogen overnight at room temperature. The toluene was then evaporated off in vacuo and the crude orange oil dissolved in ethyl acetate and washed with water, 1 HCl, IN NaOH and brine. The organic phase was dried over magnesium sulfate and the solvent vacced off.

The synthetic route of 1615-14-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY COLLEGE LONDON; POSADA, Cristina, Garcia; SELWOOD, David; GARTHWAITE, John; BAKER, David; CLUTTERBUCK, Lisa; WO2011/61469; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1003-21-0, 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 1003-21-0 as follows.

iPrMgCl (2.06 M in THF, 0.72 mL, 1.48 mmol) was added dropwise at 0 C. over 1.5 minutes to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (0.257 g, 1.60 mmol) in THF (4 mL; dried over 3 A molecular sieves) under argon. After stirring for 17 minutes, a solution of tert-butyl 4-(4-chloro-2-methoxy-3-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-6-carbonyl)piperidine-1-carboxylate (0.452 g, 0.899 mmol, Intermediate 5) and LaCl3-2LiCl (0.5 M in THF, 1.98 mL, 0.988 mmol) in THF (2 mL) was added dropwise over 2 minutes to the Grignard reagent at 0 C., and after 30 minutes the reaction was quenched with 5 M aqueous NH4Cl (1 mL). The aqueous layer was extracted with DCM (1*5 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by FCC (0-10% MeOH in DCM) to afford the title compound as a white foam. 1H NMR (400 MHz, CDCl3) delta 8.10 (br. s., 1H), 7.74 (d, J=8.59 Hz, 1H), 7.34-7.41 (m, 1H), 7.29 (s, 1H), 7.18 (s, 1H), 4.25 (br. s., 1H), 4.07 (s, 3H), 3.91-3.98 (m, 2H), 3.28-3.38 (m, 2H), 3.23 (s, 3H), 2.90 (d, J=7.07 Hz, 2H), 2.55-2.85 (m, 2H), 2.31-2.42 (m, 1H), 2.18-2.26 (m, 1H), 1.91-2.04 (m, 1H), 1.66 (br. s., 3H), 1.49-1.59 (m, 3H), 1.41 (s, 9H), 1.29-1.38 (m, 1H), 1.13-1.23 (m, 2H); MS m/e 584.8 [M+H]+.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16265-04-6, name is 2-Chloro-1H-imidazole, 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. Formula: C3H3ClN2

To a solution of 2-chloro-1H-imidazole (250 mg, 2.44 mmol) in DMF (5 mL) were added K2CO3 (1011 mg, 7.32 mmol) and tert-butyl (2-bromoethyl)carbamate (601 mg, 2.68 mmol), and the resulting mixture was stirred at 80 C. for 16 h then concentrated under reduced pressure. H2O (20 mL) was added, the mixture was extracted with EtOAc (3*10 mL), and the combined organic layers were washed with sat. aq. NaCl, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (0% to 5% MeOH in CH2Cl2) to give the title compound as a white solid (394 mg, 66%). MS (ES+) C10H16ClN3O2 requires: 245, found: 246 [M+H]+.

The synthetic route of 2-Chloro-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; JONES, Philip; CROSS, Jason Bryant; CARROLL, Christopher L.; MCAFOOS, Timothy Joseph; MANDAL, Pijus Kumar; US2019/298729; (2019); A1;,
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Imidazole | C3H4N2 – PubChem

Reference of 1792-40-1,Some common heterocyclic compound, 1792-40-1, name is 2-Methyl-5-nitro-1H-benzo[d]imidazole, molecular formula is C8H7N3O2, 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 2-methyl-5-nitro-1H-benzimidazole (0.7 g, 4 mmol), (Boc)2O (4.4 mol) and NaHCO3 (4.4 mol) in methanol (30 ml) was stirred at rt for 24 h. The solid was filtered then the solvent was evaporated and purified by column chromatography (petroleum ether/ethyl acetate, 10:1) gave 8 (0.86 g, 78%) as white solid, mp 134-136 C. 1H NMR (300 MHz, CDCl3 delta 1.43 (s, 9H, 3CH3), 2.50 (s, 3H, CH3), 7.61 (d, J = 9 Hz, 1H, H7), 8.02 (d, J = 9 Hz, 1H, H6), 8.34 (s, 1H, H4). 13C NMR (75 MHz, CDCl3 delta 14.9, 28.6, 84.1, 84.3, 85.7, 113.3, 116.8, 119.0, 137.0, 138.2, 140.1, 145.0, 148.1 ppm. MS (EI) m/z (%): 277.11 (20, M+), 176 (100, M-101). Anal. Calcd for C13H15N3O4: C, 56.31; H, 5.45; N, 15.15. Found: C, 56.50; H, 5.27; N, 15.10.

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

Reference:
Article; El-Nezhawy, Ahmed O.H.; Biuomy, Ayman R.; Hassan, Fatma S.; Ismaiel, Ayman K.; Omar, Hany A.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1661 – 1670;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 51605-32-4, The chemical industry reduces the impact on the environment during synthesis 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

To a suspension of 60percent sodium hydride (3.12 g) which had been washed before with hexane in DMF (100 ml), ethyl 4-methylimidazole-5-carbonate (10.0 g) was added by portions at 0¡ãC. The mixture was allowed to be at room temperature and stirred for 1 hour under nitrogen atmosphere, and then, 1-iodopropane (13.9 g) was added dropwise to the mixture. After the mixture was stirred for 1 hour, water was added to the mixture, and the mixture was extracted with ethyl acetate twice. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was separated and separated and purified by basic silica gel column chromatography (hexane-ethyl acetate = 3:1), to give ethyl 4-methyl-1-propylimidazole-5-carbonate (4.31 g) and ethyl 5-methyl-1-propylimidazole-4-carbonate (8.25 g). ethyl 4-methyl-1-propylimidazole-5-carbonate 1H-NMR (200 MHz, CDCl3) delta 0.91 (3H, t, J = 7.4 Hz), 1.39 (3H, t, J = 7.2 Hz), 1.69 to 1.87 (2H, m), 2.49 (3H, s), 4.19 (2H, t, J = 7.4 Hz), 4.33 (2H, q, J = 7.2 Hz), 7.44 (1H, s). ethyl 5-methyl-1-propylimidazole-4-carbonate 1H-NMR (200 MHz, CDCl3) delta 0.95 (3H, t, J = 7.4 Hz), 1.40 (3H, t, J = 7.4 Hz), 1.67 to 1.86 (2H, m), 2.54 (3H, s), 3.84 (2H, t, J = 7.4 Hz), 4.38 (2H, q, J = 7.4 Hz), 7.40 (1H, s).

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, Ethyl 5-methyl-1H-imidazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1422228; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, 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. Formula: C7H10N2O2

(1) Ethyl 4-methyl-1H-imidazole-5-carboxylate (7.5 g, 48.7mmol) was dissolved in acetonitrile (120 mE), N-bromosuccinimide (10.4 g, 58.4 mmol) was added thereto, and then themixture was stirred at room temperature for 3 hours. Afier thereaction, saturated aqueous sodium hydrogen carbonate wasadded and the mixture was extracted twice with ethyl acetate.Afier washing with saturated aqueous sodium chloride, theorganic layer was dried over anhydrous sodium sulfate. Afterconcentrating the organic layer, the residue was purified bycolunm chromatography to obtain ethyl 2-bromo-4-methyl-1 H-imidazole-5-carboxylate (3.6 g):(3H, s), 1.37 (3H, t, J=7.i Hz);j0127] iH.NMR (CDC13) oe: 4.35 (2H, q, J=7.i Hz), 2.51j0128] ESI-MS mlz=233 (M+H).

The synthetic route of Ethyl 5-methyl-1H-imidazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Teijin Pharma Limited; Maruyama, Akinobu; Kamada, Hirofumi; Fujinuma, Mika; Takeuchi, Susumu; Saitoh, Hiroshi; Takahashi, Yoshimasa; US2015/284358; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem