Tag: M.W=100-200

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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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. 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;,
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 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;,
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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Imidazole | C3H4N2 – PubChem

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;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 492-98-8, These common heterocyclic compound, 492-98-8, name is 1H,1’H-2,2′-Biimidazole, 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.

Example 4: Synthesis of (tetrakis(2-(2,4-difluorophenyl)pyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(dfppy)2BIm]2) [0243] [0244] Under argon atmosphere, into a 250 mL Schlenk flask equipped with a stirrer were placed 486 mg (0.40 mmol) of di-mu-chloro-tetrakis(2-(2,4-difluorophenyl)pyridinato) diiridium(III), 54 mg (0.40 mmol) of 2,2′-biimidazole and 80 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 1 hour. Subsequently, 111 mg (0.84 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 2 hours. After the completion of the reaction, the reaction liquid was concentrated, and then methylene chloride, water and a saturated aqueous solution of ammonium chloride were added to the resultant concentrate until pH became 7, and the organic phase was separated from the water phase. The resultant organic phase was dried with sodium sulfate, and filtered, and then the filtrate was concentrated. And then, the resultant concentrate was washed with hexane, to provide 441 mg of binuclear iridium complex (1) as a yellow solid. (Isolation yield: 86 %) [0245] The obtained binuclear iridium complex (1) was a mixture of two different types of isomers, and the abundance ratio was 60:40. The binuclear iridium complex obtained as the main product (60 %) was referred to as “binuclear iridium complex (1a)” and the binuclear iridium complex obtained as the secondary product (40 %) was referred to as “binuclear iridium complex (1b)” [0246] Additionally, the binuclear iridium complex (1) was a novel compound, which had the following properties: [0247] 1H-NMR (400MHz, C4D8O, delta (ppm)); Binuclear iridium complex (1a); 8.17 (d, 4H), 8.13-8.12 (m, 4H), 7.79-7.75 (m, 4H), 7.91-7.15 (m, 4H), 6.49-6.42 (m, 4H), 6.22 (s, 4H), 5.84-5.81 (m, 4H) Binuclear iridium complex (1b); 8.24 (d, 4H), 7.85-7.81 (m, 4H), 7.74-7.72 (m, 4H), 6.95-6.91 (m, 4H), 6.49-6.42 (m, 4H), 6.24 (s, 4H), 5.77-5.74 (m, 4H) FD-MS (M/Z): 1276 (M+)

Statistics shows that 1H,1’H-2,2′-Biimidazole is playing an increasingly important role. we look forward to future research findings about 492-98-8.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 2466-76-4, The chemical industry reduces the impact on the environment during synthesis 2466-76-4, name is 1-(1H-Imidazol-1-yl)ethanone, I believe this compound will play a more active role in future production and life.

Step Three; N-((1S, 2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-{[(4S)-6- hydroxy-3, 4-dihydro-2H-chromen-4-yl] amino} propyl) acetamide; OH H H OH H H2N N N-N 2HCl \ 1. 2 equiv. acetylimidazole 2HCl ~ + l 1. 2equiv. acetinidazole 11 41 A 2. K2CO3, MeOH, H20/==\ F HOpercent F HO/ F F To a solution of the product from step 2 (200 mg, 0.43 mmol) in methylene chloride (5 mL) was added triethylamine (217 mg, 2.15 mmol) followed by 1-acetylimidazole (95 mg, 0.86 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and water (3 mL) and treated with potassium carbonate (300 mg, 2.17 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate (3 x 50 mL). The combined extracts were washed with saturated sodium chloride, and dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 0-5percent methanol/methylene chloride provided the desired product (85 mg, 49percent) as a white foam.

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, 1-(1H-Imidazol-1-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; PHARMACIA & UP JOHN COMPANY; WO2005/95326; (2005); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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.

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 3.59 g (9.8 mmol) of 1-octadecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 3.00 g (69%). Mp=56-58 C. IR-spectrum (KBr), cm-1: 3325, 3140, 3080, 2915, 2850, 1565, 1472,1378, 1165,1071, 871, 721. 1H NMR spectrum, 400 MHz (CDCl3), delta,ppm, J/Hz: 0.87 t (3H, J=7.0), 1.24-1.32m (30 H), 1.89-1.92m (2 H),3.98 t (2H, J=4.27), 4.26 t (2H, J=7.6), 4.53 t (2H, J=4.90), 7.31 s(1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 365.5 [M-Br]+.Calculated, %: C23H45 N2 OBr: C 62.00; H 10.18; N 6.29; Br 17.93;found, %: C 61.75; H 10.43; N 6.22; Br 17.58.

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

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
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Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. Product Details of 75370-65-9

Preparation of 1-(4-(dimethylamino)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea 4-(aminomethyl)-N,N-dimethylbenzenamine 2i (1 g, 6.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (1 g, 6.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 350 mg of a white solid. Yield = 16% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.18 (2H, d, J = 5.6 Hz), 6.58 (2H, m), 6.69 (2H, d, J = 8.8 Hz), 6.86 (2H, m), 7.14 (2H, d, J = 8.8 Hz), 8.18 (1H, s), 9.98 (1H, bs), 10.58 (1H, bs); [M+1] 326.5 (C17H19N5O2 requires 325.37).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, 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 3314-30-5, name: 1H-Benzo[d]imidazole-2-carbaldehyde

Example 5 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone (Indo 5) 0.15 g (0.5 mmol) 5-(2-methylphenylaminosulfo)-2-indolone and 0.10 g (0.685 mmol) 1H-benzimidazol-2-formaldehyde were suspended in 6 mL anhydrous ethanol, followed by addition of 2 drops of piperidine. The mixture was heated and refluxed in an oil bath for 30 min. A large quantity of yellow solid was precipitated, filtered, and washed with anhydrous ethanol, to obtain 0.12 g pale yellow solid, with a yield of 55.8percent. Analytical result by NMR spectroscopy: 1H-NMR (DMSO-d6) delta (ppm): delta13.82 (s, 1H), 11.70 (s, 1H), 9.44 (s, 1H), 8.20 (s, 1H), 8.00 (s, 1H), 7.82 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=8.0 Hz), 7.61 (dd, 1H, J=16.8 Hz), 7.38 (t, 1H), 7.30 (t, 1H), 7.00-7.15 (m, 5H), 2.09 (s, 3H). ESI-MS m/z: 429 [M-H]+ (100). Analysis showed that, the pale yellow solid is 3-(1H-benzimidazol-2-methylene)-5-(2-methylphenylaminosulfo)-2-indolone, the structural formula of which is shown in Formula I, wherein R1 is 2-methylphenylaminosulfo, and R2 is hydrogen.

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]imidazole-2-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INSTITUTE OF RADIATION MEDICINE, CHINA ACADEMY OF MILITARY MEDICAL SCIENCES PLA; Yang, Xiaoming; Wang, Lin; Li, Changyan; Zhan, Yiqun; Liu, Jing; Luo, Teng; Yan, Haiyan; Zhang, Shouguo; Li, Wei; Wen, Xiaoxue; Peng, Tao; Li, Lu; (18 pag.)US2016/151334; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem